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Yao, Hua et al. published their research in Organic Letters in 2022 | CAS: 1190314-60-3

5-Chloro-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (cas: 1190314-60-3) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Product Details of 1190314-60-3

Cyanomethylation of the Benzene Rings and Pyridine Rings via Direct Oxidative Cross-Dehydrogenative Coupling with Acetonitrile was written by Yao, Hua;Zhong, Xiaoyang;Wang, Bingqing;Lin, Sen;Yan, Zhaohua. And the article was included in Organic Letters in 2022.Product Details of 1190314-60-3 The following contents are mentioned in the article:

A novel and efficient approach for the amine-directed dehydrogenative C(sp₂)-C(sp₃) coupling of arylamines RNH₂ (R = Ph, 5-chloropyridin-2-yl, pyrazin-2-yl, etc.) with acetonitrile was reported by using FeCl₂ as the catalyst. Arylamines react with inactive acetonitrile to form the corresponding arylacetonitriles R¹CH₂CN (R¹ = 2-amino-5-chloropyridin-3-yl, 2-aminophenyl, 6-amino-1,3-benzothiazol-7-yl, etc.) in moderate to good yields. This protocol features nontoxic iron catalysis, efficient atom economy, nonprefunctionalized starting materials, good regioselectivity, and excellent compatibility of functional groups and aromatic rings, providing a novel, straightforward, and green approach toward arylacetonitriles. This study involved multiple reactions and reactants, such as 5-Chloro-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (cas: 1190314-60-3Product Details of 1190314-60-3).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Meyer, Horst et al. published their research in Liebigs Annalen der Chemie in 1981 | CAS: 15540-90-6

4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). SDS of cas: 15540-90-6

Malonodiamidines. III. Synthesis and condensation reactions of 1,2,3,4,6,7-hexahydro-7-imino-1,4-dimethyl-5H-1,4-diazepin-5-one was written by Meyer, Horst. And the article was included in Liebigs Annalen der Chemie in 1981.SDS of cas: 15540-90-6 The following contents are mentioned in the article:

[EtOC(:NH)]₂CH₂ reacted with MeNHCH₂CH₂NH₂ to give 2,2′-methylenebis(imidazoline), whereas with MeNHCH₂CH₂NHMe the diazepines I (X = NH, O) were obtained, depending on the amount of H₂O in the reaction. I (X = O) underwent cyclocondensations with mono- and diketones to give II (RR¹ = N:CMeCH:CMe, NHCR²:CR³CHR⁴; R² = Ph, C₆H₄NO₂-3; R³ = CO₂Et, H; R⁴ = Me, Ph) and III (R⁵ = H, 8-Me, 8-Br, R⁶ = H; R⁵ = 8-Me, 9-Cl, 7-Cl, R⁶ = Me). This study involved multiple reactions and reactants, such as 4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6SDS of cas: 15540-90-6).

Baxter, Gary J. et al. published their research in Australian Journal of Chemistry in 1975 | CAS: 15540-90-6

4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Reference of 15540-90-6

Methyleneketenes and methylenecarbenes. V. Condensation of ketones with isopropylidene malonate catalyzed by titanium tetrachloride and synthesis of a dibenzofuran was written by Baxter, Gary J.;Brown, Roger F. C.. And the article was included in Australian Journal of Chemistry in 1975.Reference of 15540-90-6 The following contents are mentioned in the article:

The TiCl4-pyridine-THF reagent of Lehnert will effect direct condensation of some aromatic ketones RCOR1(R = Ph, o-tolyl, 2,5-dimethyl-3-furyl; R1 = Me, Ph, Co2Me, piperidinocarbonyl; RR1 = 2,2′-biphenylylene) with isopropylidene malonate (Meldrum’s acid) to give I. The synthetic value of this reaction is explored in a synthesis of 7-methoxy-9-methyldibenzofuran-3-ol involving pyrolysis of I (R = 2,5-dimethyl-3-furyl), formylation of II with Cl2CHOMe and SnCl4, conversion of III to the 6-MeO analog. condensation with isopropylidene malonate, and pyrolysis of the product. A 1,9-dimethyldibenzofuran related to strepsilin could not be obtained in the same way. This study involved multiple reactions and reactants, such as 4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6Reference of 15540-90-6).

Zhang, Nanjing et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2016 | CAS: 1000343-16-7

5-Fluoro-6-methyl-1H-indole (cas: 1000343-16-7) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Recommanded Product: 5-Fluoro-6-methyl-1H-indole

Discovery of 2-(4-sulfonamidophenyl)-indole 3-carboxamides as potent and selective inhibitors with broad hepatitis C virus genotype activity targeting HCV NS4B was written by Zhang, Nanjing;Turpoff, Anthony;Zhang, Xiaoyan;Huang, Song;Liu, Yalei;Almstead, Neil;Njoroge, F. George;Gu, Zhengxian;Graci, Jason;Jung, Stephen P.;Pichardo, John;Colacino, Joseph;Lahser, Fred;Ingravallo, Paul;Weetall, Marla;Nomeir, Amin;Karp, Gary M.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2016.Recommanded Product: 5-Fluoro-6-methyl-1H-indole The following contents are mentioned in the article:

A novel series of 2-(4-sulfonamidophenyl)-indole 3-carboxamides was identified and optimized for activity against the HCV genotype 1b replicon resulting in compounds with potent and selective activity. Further evaluation of this series demonstrated potent activity across HCV genotypes 1a, 2a and 3a. Compound I had reduced activity against HCV genotype 1b replicons containing single mutations in the NS4B coding sequence (F98C and V105M) indicating that NS4B is the target. This novel series of 2-(4-sulfonamidophenyl)-indole 3-carboxamides serves as a promising starting point for a pan-genotype HCV discovery program. This study involved multiple reactions and reactants, such as 5-Fluoro-6-methyl-1H-indole (cas: 1000343-16-7Recommanded Product: 5-Fluoro-6-methyl-1H-indole).

Wang, Minghua et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2015 | CAS: 1190314-60-3

5-Chloro-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (cas: 1190314-60-3) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Product Details of 1190314-60-3

Synthesis and antitumor activity of 5-(5-halogenated-2-oxo-1H-pyrrolo[2,3-b]pyridin-(3Z)-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamides was written by Wang, Minghua;Ye, Cheng;Liu, Mingliang;Wu, Zhaoyang;Li, Linhu;Wang, Chunlan;Liu, Xiujun;Guo, Huiyuan. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2015.Product Details of 1190314-60-3 The following contents are mentioned in the article:

We report herein the design and synthesis of a series of novel 5-halogenated-7-azaindolin-2-one derivatives containing a 2,4-dimethylpyrrole moiety. Nine target compounds with ≥70% inhibition against MCF-7 at 30 μM were further evaluated for their in vitro antitumor activity against seven human cancer cell lines by SRB assay. Results reveal that some compounds have potent antitumor activity, and the most active I (IC₅₀s: 4.49-15.39 μM) was found to be more active than Sunitinib (IC₅₀s: 4.70->30 μM) against all of the tested cancer cell lines. This study involved multiple reactions and reactants, such as 5-Chloro-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (cas: 1190314-60-3Product Details of 1190314-60-3).

5-Chloro-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (cas: 1190314-60-3) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Product Details of 1190314-60-3

Rana, Sandeep et al. published their research in Journal of Medicinal Chemistry in 2016 | CAS: 15540-90-6

4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Electric Literature of C10H9NO2

Isatin Derived Spirocyclic Analogues with α-Methylene-γ-butyrolactone as Anticancer Agents: A Structure-Activity Relationship Study was written by Rana, Sandeep;Blowers, Elizabeth C.;Tebbe, Calvin;Contreras, Jacob I.;Radhakrishnan, Prakash;Kizhake, Smitha;Zhou, Tian;Rajule, Rajkumar N.;Arnst, Jamie L.;Munkarah, Adnan R.;Rattan, Ramandeep;Natarajan, Amarnath. And the article was included in Journal of Medicinal Chemistry in 2016.Electric Literature of C10H9NO2 The following contents are mentioned in the article:

Design, synthesis, and evaluation of α-methylene-γ-butyrolactone analogs and their evaluation as anticancer agents is described. SAR identified a spirocyclic analog I that inhibited TNFα-induced NF-κB activity, cancer cell growth and tumor growth in an ovarian cancer model. A second iteration of synthesis and screening identified II which inhibited cancer cell growth with low-μM potency. Our data suggest that an isatin-derived spirocyclic α-methylene-γ-butyrolactone is a suitable core for optimization to identify novel anticancer agents. This study involved multiple reactions and reactants, such as 4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6Electric Literature of C10H9NO2).

Ablondi, Frank et al. published their research in Journal of Organic Chemistry in 1952 | CAS: 15540-90-6

4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Application In Synthesis of 4,7-Dimethylindoline-2,3-dione

An Antimalarial alkaloid from hydrangea. XV. Synthesis of 5-, 6-, 7-, and 8-derivatives with no identical substituents was written by Ablondi, Frank;Gordon, Samuel;Morton, John II;Williams, J. H.. And the article was included in Journal of Organic Chemistry in 1952.Application In Synthesis of 4,7-Dimethylindoline-2,3-dione The following contents are mentioned in the article:

To study the effect of substituents in the C₆H₆ ring on the antimalarial activity and chemotherapeutic index of the DL-form of the hydrangea alkaloid, a series of derivatives with 2 identical substituents in the benzene ring are synthesized by converting, according to Marvel and Hiers (C.A. 20, 193), the appropriate R₂C₆H₃NH₂ into the R₂C₆H₃NHCOCH:NOH (I) (Table F) which, on ring closure with 86% H₂SO₄, give the corresponding isatins (II) (Table G). Oxidation of II with alk. peroxide gives the disubstituted o-H₂NC₆H₄CO₂H (III) (Table H) which, on fusion with HCONH₂ (see preceding abstract), give the corresponding disubstituted 4(3H)-qainazolones (IV) (Table I). Condensation of 1-carbethoxy-2-(3-bromoacetonyl)-3-methoxypiperidine with the appropriate IV gives the disubstituted 3-[2-oxo-3-(1-carbethoxy-3-methoxy-2-piperidyl)propyl]-4(3H)-quinazolones (V) which, hydrolyzed with 6 N HCl, give the corresponding 3-[2-oxo-3 – (3-methoxy-2-piperidyl)propyl]-4(3H)-quinazolones (VI). Demethylation of VI then gives the corresponding 3-hydroxy-2-piperidyl derivatives (VII) (VIa, R = H). The IV, V, VI, and VII are listed in Table I. Cyclization of 55 g. 3,4-Me.₂C₆H₃NHCOCH:NOH with 292 cc. 96% H₂SO₄ and 29 cc. H₂O, solution of the isatin mixture in 1.2 l. H₂O and 310 cc. 10% NaOH, dropwise addition of 12 N HCl to the filtered solution until turbid, and then addition of 4-cc. portions of acid and separation of the precipitate after each addition give 12.6 g. crude 4,5-dimethylisatin. The 4th addition gives no precipitate and strong acidification of the mother liquor gives 23.3 g. 5,6-dimethylisatin. Treating 21.5 g. 4-chloroisatin 4 h. at 50° in 440 cc. AcOH with 20 cc. SO₂Cl₂ and a crystal of iodine gives 60% 4,5-dichloroisatin. In the same way 6-chloroisatin gives 5,6-dichloroisatin. Adding 16.2 g. NaNO₂ in small portions to 25 g. 3,5,2-Me₂(H₂N)C₆H₂NO₂ in 70 cc. 6 N HCl at 0-5° with stirring and adding the diazonium solution to 35.6 g. NaCN and 34.5 g. NiCl₂.H₂O in 230 cc. H₂O with warming on a steam bath 45 min. give 79% 3,5,2-Me₂(NC)C₆H₂NO₂, m. 125-8° which (18.7 g.), heated with 50 cc. 80% H₂SO₄ 5 h. on a steam bath and poured onto ice, gives 52% 4,6,2-Me₂(O₂N)C₆H₂CONH₂; Table F. Disubstituted α-isonitrosoacetanilides (I); Reaction time, Yield, M.p.,;R₂, (min.), %, °C.; 3,4-Di-Me, 2, 84, 179-80^a; 2,5-Di-Me, 5, 33, 151-3; 2,4-Di-Me, 8, 55, 158-9; 2,3-Di-Me, 3, 64, 131-2; 2,5-Di-Cl, 15, 22, 166-8; 3,5-Di-Br, 15, 11, 197-200; 3,4-(CH₂)₄_^–, 120, 87, 147-50; (a) Decomposition Table G., Disubstituted isatins (II); Yield, M.p., R₂, Color, %, °C.; 4,5-Di-Me, red, 25, 225-6; 4,7-Di-Me, orange, 75, 260-4; 5,6-Di-Me, red, 46, 214-15; 5,7-Di-Me, orange, 91, 228-31; 6,7-Di-Me, orange, 57, 230-2; 4,5-Di-Cl, red, 60, 243-5; 4,7-Di-Cl, 99, 239-41; 5,6-Di-Cl, orange-red, 68, 264-8^a; 4,6-Di-Br, orange, 88, 254-6; 4,5-(CH₂)₄_^–, orange, 32, 188-90^a; 5,6-(CH₂)₄_^–, orange, 17, 176-85^a; (a) Decomposition; Table H. Disubstituted anthranilic acids; Yield, M.p.a,; R₂, %, °C.; 5,6-Di-Me, 65, 140-1; 4,6-Di-Me, 91, 160-1; 3,6-Di-Me, 58, 111-13; 4,5-Di-Me, 81, 213-14; 3,5-Di-Me, 65, 188-9; 3,4-Di-Me, 69, 184-6; 5,6-Di-Cl, 59, 165-7; 3,6-Di-Cl, 59, 148-50; 4,5-Di-Cl, 99, 208; 3,5-Di-Cl, 39, 230-1; 4,6-Di-Br, 73, 170-1; 5,6-(CH₂)₄_^–, 62, 114; 4,5-(CH₂)₄_^–, 86, 171-3; (a) Decomposition (VIII), m. 169-71°. Reduction of 12.9 g. VIII in 100 cc. Methyl Cellosolve 20 min. with 1 g. Pd-charcoal at 2-3 atm. H gives 91% 4,6,2-Me₂(H₂N)C₆H₂CONH₂, m. 160-1°. Adding 25 cc. SO₂Cl₂, over a period of 15 min. to 20 g. o-H₂NC₆H₄CO₂H in 500 cc. AcOH at 40°, stirring the mixture 2 h., and extracting the precipitate with 15% HCl on a steam bath give 39% 3,5,2-Cl₂(H₂N)C₆H₂CO₂H, m.230-1°. This study involved multiple reactions and reactants, such as 4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6Application In Synthesis of 4,7-Dimethylindoline-2,3-dione).

4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Application In Synthesis of 4,7-Dimethylindoline-2,3-dione

Sandmeyer, T. et al. published their research in Helvetica Chimica Acta in 1919 | CAS: 15540-90-6

4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Product Details of 15540-90-6

Isonitrosoacetanilides and their condensation to form isatin derivatives was written by Sandmeyer, T.. And the article was included in Helvetica Chimica Acta in 1919.Product Details of 15540-90-6 The following contents are mentioned in the article:

Hydroxylaminesulfonic acid solution (A) was prepared by adding rapidly with stirring 627 g. NaHSO₃ to 84 g. NaNO₂ in 500 cc. H₂O containing 300 g. ice. After 1.5 hrs. a cold solution of 66 g. concentrated H₂SO₄ in 66 g. H₂O is added during the course of 2 hrs. until the solution is acid to congo paper; after 2 days the reaction is completed. Isonitrosoacetanilide (B) is prepared by boiling 3-4 hrs. under reflux 450 g. of A, adding 10 g. PhNH₂, 350 g. H₂O, 16.5 g. CCl₃CHO.H₂O and continuing the boiling for 1 hr. longer. On cooling rapidly the light yellow crystals of B sep., are filtered and washed with H₂O; they m. 175° (decomposition), are readily soluble in Et₂O or EtOH, slightly in cold H₂O or PhH; acids precipitate it unchanged from alk. solutions Isonitrosoacet-p-chloroanilide (C) is prepared by boiling under reflux for several hrs. 450 g. of A, mixing a 100-50 g. portion into a paste with 12.75 g. p-ClC₆H₄NH₂, adding the paste to the remainder of A, diluting with 300 g. H₂O and then boiling for 0.75 hr. with 16.5 g. CCl₃CHO.H₂O. The crystals of C which sep. on cooling are dissolved in dilute NaOH, dilute HCl is added nearly to neutralization and the solution filtered. C is obtained on the addition of acid as a white, crystalline precipitate which is filtered and washed with H₂O; it m. 165°, is slightly soluble in H₂O, fairly in Et₂O and readily in EtOH; yield, 14.3 g. The following derivatives were obtained in the same way from the corresponding aromatic amines and the m. p. refers to the uncrystd. reaction product: o-toluide, 121°; m-toluide, 146°; p-toluide, 162°; m-xylide, 161°; p-xylide, 151°; o-aniside, 140°; p-phenetide, 195°; methylanilide, 145°; ethylanilide, 160°; benzylanilide, 142°; o-chloroanilide, 150°; m-chloroanilide, 154°; 2,5-dichloroanilide, 163°; 3,4-dichloroanilide, 158°; 3,5-dichloroanilide, 185°; 5-chloro-2-toluide (Me = 1), 167°; 4-chloro-2-toluide, 148°; 6-chloro-3-toluide, 187°; 4-chloro-3-toluide, 134°; 2-chloro-4-toluide, 177°; 3-chloro-4-toluide, 188°; 4-chloro-2-aniside (MeO = 1), 182°; p-bromoanilide, 167°; 2,4-dibromoanilide, 215°; anthranilic acid, 208°. Isatin (D) was prepared by adding gradually with stirring 10 g. B to 50 g. of concentrated H₂SO₄ at 60° and keeping the temperature at all times below 65°; after B has been added and is in solution, the temperature, is raised to 75° for 10-5 min.; the solution is cooled and immediately diluted with 160 g. cold H₂O; the yellow-red crystals of D which sep. are filtered and washed with H₂O; these crystals show all the characteristic tests for D and m. 197°. In the same way by modifying the temperature the following isonitrosoacetanilides were converted into isatin derivatives; at 55-60° during addition and at 65-70° at completion, methyl and ethylanilides; at 60-5° and subsequently at 70-5°, o- and p- toluides and o- and p-xylides; at 80-5° and subsequently at 95°, o- and m-chloroanilides, 4-chloro-2-toluide, 4-chloro-3-toluide, 2-chloro-4-toluide, 4-chloro-2-aniside; at 90-5° subsequently 105°, 3-chloro-4-toluide, 5-chloro-2-toluide, 6-chloro-3-toluide, p-chloro-anilide, 2,5-and 3,5-dichloroanilides; at 95-100°, subsequently 110°, 3,4-dichloro-anilide, p-bromoanilide, anthranilic acid. The isatin derivatives from o-aniside, p-phenitide and 2,4-dibromoanilide could not be prepared by this reaction; a mixture of two isomers is obtained when both free o-positions are not the same, e. g., m-toluide or 3,4-dichloroanilide. The following were prepared by this reaction and the m. p. refers to the uncrystd. material; mixture of 4- and 6-methylisatins, orange-yellow, 143°; 4,7-dimethylisatin, orange-yellow, 250°; 7-chloroisatin, red-brown, 175°; mixture of 4- and 6-chloroisatins, orange-yellow, 212°; mixture of 4-chloro-7-methylisatin, orange-yellow, 4,5- and. 5,6-dichloroisatins, yellow-red 200°; 4,6-dichloroisatin, citron-yellow, 250°; 273°; 5-chloro-7-methylisatin, yellow-brown, 265°; mixture of 4-chloro-5-methyl- and 5-methyl-6-chloroisatins, red, 205°; 4-methyl-7-chloroisatin, orange-yellow, 252°; 4-chloro-7-methoxyisatin, red, 240°; isatin-7-carboxylic acid, brown-yellow, 235°. Many of the yields were quant. Application for patents has been made. This study involved multiple reactions and reactants, such as 4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6Product Details of 15540-90-6).

Giovannini, E. et al. published their research in Helvetica Chimica Acta in 1957 | CAS: 15540-90-6

4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Name: 4,7-Dimethylindoline-2,3-dione

Reactivity of the carbonyl group and of dehydrogenation activity of isatin compounds. II was written by Giovannini, E.;Portmann, P.;Johl, A.;Schnyder, K.;Knecht, B.;Zen-Ruffinen, H. P.. And the article was included in Helvetica Chimica Acta in 1957.Name: 4,7-Dimethylindoline-2,3-dione The following contents are mentioned in the article:

The dehydrogenation activity of many mono- and disubstituted derivatives of isatin (I) expressed as time of decolorization of a methylene blue (II) solution according to Langenbeck (C.A. 21, 2126) have been measured and tabulated as relative activities to that of I (100), using 10^-4 or 2 × 10^-5 mole compound in 5 cc. pyridine and 2 cc. standard aqueous solution [2 g. DL-MeCH(NH₂)CO₂H (III), 0.3737 g. II, and 10 cc. AcOH made up to 100 cc.] (isatin substituent, m.p., decoloration time (min.) with 10^-4 and 2 × 10^-5 mole, relative dehydrogenation activity given): H, 200°, 10, 50, 100; 4-Me, 190-2°, > 1320, -, < 0.75; 5-Me, 186-7°, 11, 50, 95; 6-Me, 190-1°, 19, 72, 61; 7-Me, 266°, -, 31, 161; 4-Cl, 259-60°, 113, -, 8.8; 5-Cl, 251-3°, 7, 42, 131; 6-Cl, 263°, 8, -, -; 7-Cl, 188-90°, 6, 33, 159; 4-NO₂, 245°, > 900, -, < 1.1; 5-NO₂, 253°, 12, 68, 88; 6-NO₂, 288-90°, 7, 48, 123; 7-NO₂, 237°, -, 42, 119; 4-NH₂, 254-5°, > 900, -, < 1.1; 5-NH₂, above 330°, 12, 65, 80; 7-NH₂, above 330°, -, 52, 96; 4-HO, 260° (decomposition), 73, -, 13.7; 5-HO, above 290° (decomposition), 9, -, 111; 6-HO, above 325° (decomposition), 127, -, 7.8; 5-MeO, 201-2°, 9, 43, 114; 6-MeO, 229-30°, 69, -, 14.4; 7-MeO, 240-2°, 7, 33, 147; 4-CO₂H, 285°, -, 1.5, 3300; 5-CO₂H, 295°, 7, 32, 150; 6-CO₂H, 328-30°, -, 28, 178; 7-CO₂H, 277°, -, 32, 156; 4-SO₃H, 183° (decomposition), 4, -, 250; 5-SO₃H, 145-7°, 19, -, 52; 6-SO₃H, above 290° (decomposition), 15, -, 67; 7-SO₃H, m. above 350° (decomposition), 19, -, 52. Substituents in the 4-position have a great influence, in one sense or another, on the dehydrogenation activity of I and probably on the activity of the 3-CO group. The effect of the 4-CO₂H group is not due to its acid character as shown by the relative dehydrogenation activities of the 4-HO and 4-SO₃H substituted compounds The effect of double substitution was examined: 4,6-Me₂, 241-3°, > 900, -, < 1.1; 4,7-Me₂, -, > 900, -, < 1.1; 5,6-Me₂, 212-13°, 20, -, 50; 4,7-Me(CO₂H), 258-60°, > 900, -, < 1.1; 7,4-Me(CO₂H), 295°, -, 1.5, 3300; 4,7-(CO₂H)₂, 303-5°, -, 3.5, 1430; 4,7-Cl₂, 246°, 89, -, 11.2; 5,6-(HO)₂, 290° (decomposition), 230, -, 4.3; 5,6-Cl(HO), 284-6°, 236, -, 4.2; 5.6-(MeO)₂, 252°, 75, -, 13.3; 5,6-CH₂O₂, 284°, 60, -, 16.6. The inactivation caused by the 4-Me group persists. The effect of 2 activating groups is not additive but groups with contrary effects may give an intermediate value. Since the inactivation caused by some 4-substituents might be attributable to steric effects, the dehydrogenation activities with H₂NCH₂CO₂H (IV) have been compared with those with III [isatin substituent, times (min.) of decolorization with III and IV, ratios of activity (III/IV) given]: H, 10, 4, 2.5; 4-Me, > 1310, 108, > 13; 5-Me, 11, 4, 2.7; 6-Me, 18, 7, 2.5; 4,6-Me₂, > 900, 205, > 4.4; 4,7-Me₂, > 900, 131, > 6.9; 4-Cl, 113, 12, 9.4; 4-NO₂, > 900, 280, > 3.2; 4-CO₂H, 1.5, 0.75, 2. The activity of 4-methylisatin is less than that of the other isomers against IV and no explanation is offered for the activity of 4-carboxyisatin. This study involved multiple reactions and reactants, such as 4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6Name: 4,7-Dimethylindoline-2,3-dione).

Mix, Hermann et al. published their research in Chemische Berichte in 1956 | CAS: 15540-90-6

4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Application of 15540-90-6

Organic catalysts. XL. Synthetic dehydrogenases. 8 was written by Mix, Hermann;Krause, Hans Walter. And the article was included in Chemische Berichte in 1956.Application of 15540-90-6 The following contents are mentioned in the article:

Some isatins, CMe:CH.CH:CR.C:C.NH.CO.CO (I), and N-(7-methylisatin-4-carbonyl)amino acid Et esters (II), substituted in the 4-position, are prepared and tested for their dehydrogenase activity. Treating p-MeC₆H₄CO₂H with fuming HNO₃ yields 4,3-Me(O₂N)C₆H₃CO₂H, m. 188-9°, which, reduced with Raney Ni in dioxane at 120° and 100 atm., gives 90% 4,3-Me(H₂N)C₆H₃CO₂H (III), m. 162°. Heating 5 g. III in 150 cc. H₂O containing 2 cc. concentrated H₂SO₄ with 5.5 g. CCl₃CHO.H₂O (IV) and 6.5 g. (HONH₂)₂.H₂SO₄ (V) yields 3-isonitrosoacetamido-4-methylbenzoic acid which (10 g.), heated in 22 cc. concentrated H₂SO₄ at 85-90° and kept 0.5 hr. at 95-100°, gives 72% I (R = CO₂H) (VI), yellow-red needles, m. 278-80°; Et ester, prepared by heating 5 g. VI in 150 cc. EtOH-HCl 0.5 hr. on a water bath and chromatographing over Al₂O₃, orange rods, m. 205°. Heating 5 g. 4,3-Me(H₂N)C₆H₃CN, m. 81°, 6.3 g. IV, and 7.5 g. V in 430 cc. H₂O and 3 cc. concentrated H₂SO₄ gives 2-2.5 g. isonitroso compound which, heated with concentrated H₂SO₄, yields I (R = CONH₂), brick-red crystals, decompose above 270°. Adding 0.94 cc. ClCO₂Et dropwise to a solution of 2 g. VI and 2.28 g. Bu₃N in 20 cc. CHCl₃ at -5°, stirring the mixture 0.5 hr. at -5°, then adding 900 mg. PhNH₂, and stirring the mixture 12 hrs. give I (R = CONHPh), small red rods, m. 308°; I (R = CONEt₂), light red leaflets, m. 192°. The following II are prepared (amino acid given): alanine, light red rods, m. 254°; norvaline, light red leaflets, m. 220°; α-aminobutyric acid, red leaflets, m. 218-19°; glutamic di-Et ester, red needles, m. 171-2°; glutamic mono-Et ester, long red needles, m. 186-7°; phenylalanine, red needles, m. 225-6°; tryptophan Me ester, purple crystals, m. 254°. Treating 1.2 g. 2,4-Me₂C₆H₃NH₂ in 30 cc. H₂O and 1.16 g. concentrated H₂SO₄ with 1.7 g. IV and 1.9 g. V yields isonitrosoacetamido-p-xylene which, added to 10 cc. concentrated H₂SO₄ at 65-7° and the mixture heated 20 min. at 65-70°, gives 4,7-dimethylisatin, yellow-red precipitate, m. 261°. Reduction of 4,3-Me(O₂N)C₆H₃NHAc with Raney Ni at 120° and 100 atm. gives 100% 3,4-Me(H₂N)C₆H₃NHAc, m. 159°, which (6 g.), stirred 4-5 hrs. at 36-40° with 6 g. IV and 7.2 g. V, yields 3-isonitrosoacetamido-4-methylacetanilide. Heating the latter 45 min. in 10 cc. concentrated H₂SO₄ at 95-100° gives 4-amino-7-methylisatin, light red needles, charring above 310°. The dehydrogenase activity of these compounds has been tested by measuring the time required to decolorize a solution of 2 × 10^-5 moles methylene blue and 2.25 × 10^-4 moles DL-alanine in 71% HCONMe₂ at 40°. The results, given in a table, show that V is the most active catalyst. The introduction of the Me group at the 7-position has no effect on the dehydrogenation velocity. For the calculation of the partial velocities of the catalysis the P_S curves of some of the compounds are given. This study involved multiple reactions and reactants, such as 4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6Application of 15540-90-6).