February 2023 - Page 98 of 117 - Indole Building Blocks

Ludt, Robert E. et al. published their research in Journal of Organic Chemistry in 1971 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. 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). Application of 5388-42-1

Effect of tetramethylethlylenediamine on the metalation of N-methyl and N-phenylbenzylamine with n-butyllithium. Deuteration and electrophilic condensations of intermediate lithioamines. Cyclodehydrations to give N-substituted isoindolines was written by Ludt, Robert E.;Hauser, Charles R.. And the article was included in Journal of Organic Chemistry in 1971.Application of 5388-42-1 This article mentions the following:

PhCH2NHMe underwent dimetalation with BuLi-Me2NCH2CH2NMe2 (TMEDA) predominantly at the N and the o-benzyl positions as evidenced by deuteration studies. The intermediate o-LiC6H4CH2NMeLi was condensed with BzPh, BzH, cyclohexanone, BzMe, and BzEt. The resulting o-carbinolamines from the BzPh and BzH condensations underwent acid-catalyzed cyclodehydration to form N-methylisoindoline derivatives, while the ortho codensation products from the latter 3 ketones underwent acid-catalyzed linear dehydration reactions, rather than cyclodehydration to form isoindolines. N-Phenylbenzylamine was similarly dimetalated at the N and o-benzyl positions with TMEDA activated BuLi. o-Carbonyl addition reactions of the dilithio amine intermediate with CO2, BzPh, BzH, and 9-fluorenone resulted in an acid and o-carbinolamines, which were readily cyclodehydrated to N-phenylphthalimidine and N-phenylisoindoline derivatives In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Application of 5388-42-1).

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

Yuan, Yu-Chao et al. published their research in Journal of Organic Chemistry in 2019 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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 5388-42-1

C-H Bond Alkylation of Cyclic Amides with Maleimides via a Site-Selective-Determining Six-Membered Ruthenacycle was written by Yuan, Yu-Chao;Goujon, Marion;Bruneau, Christian;Roisnel, Thierry;Gramage-Doria, Rafael. And the article was included in Journal of Organic Chemistry in 2019.Product Details of 5388-42-1 This article mentions the following:

The first example of a ruthenium-catalyzed C-H bond alkylation via six-membered ruthenacycles is presented. This is disclosed for the C-H bond alkylation of biol. relevant cyclic amides with maleimide derivatives The cyclic tertiary amide core acted as a directing group (DG) enabling formation of six-membered cycloruthenated species responsible for the control of the regio- and site selectivity of the reaction as well as the excellent functional group tolerance. Unexpectedly, cyclic amides were found to be better DGs than pyridine-containing ones or cyclic imides for this type of C-H bond functionalization. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Product Details of 5388-42-1).

Nigovic, Biljana et al. published their research in Acta Crystallographica, Section B: Structural Science in 1996 | CAS: 1912-45-4

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Synthetic Route of C10H8ClNO2

Structural studies on monohalogenated derivatives of the phytohormone indole-3-acetic acid (auxin) was written by Nigovic, Biljana;Kojic-Prodic, Biserka;Antolic, Snjezana;Tomic, Sanja;Puntarec, Vitomir;Cohen, Jerry D.. And the article was included in Acta Crystallographica, Section B: Structural Science in 1996.Synthetic Route of C10H8ClNO2 This article mentions the following:

The physiol. properties of the phytohormone (auxin) indole-3-acetic acid (IAA) and its ring substituted derivatives have so far been rationalized by a number of contradictory hypotheses based on incomplete structural data deduced mainly by inspection of mol. models. To give more evidence for structure-activity relations of monohalogenated IAA’s, the mol. structures of the natural auxin 4-Cl-IAA as well as 5-Cl-IAA, 6-Cl-IAA, 7-Cl-IAA and 5-Br-IAA are compared, as revealed by x-ray anal., and mol. mechanics and dynamics. The influence of the substitution site and the size of the halogen atom and bioactivity is discussed. The typical structural feature of the mols. studied is the slight distortion of part of the indole nucleus around C7: bond length C6-C7 1.368(6) 脜 and C6-C7-C71 117.6(3)掳 (average values of five structures and seven mols.). The conformations of monohalogenated indole-3-acetic acid mols., characteristic for auxins, are defined by rotations about two bonds only: one describes the relative orientation of a side chain towards the indole moiety and the 2nd the orientation of the carboxylic group. The results of x-ray structure anal., and mol. mechanics and dynamics revealed the folded shape of the mols. in all compounds studied. Ab initio calculations showed that the planar conformation can be adopted as well. Crystal data at 297 K for 4-Cl-IAA, 6-Cl-IAA, 7-Cl-IAA and 5-Br-IAA, and at 220 K for 5-Cl-IAA are as follows: 4-Cl-IAA, monoclinic, space group P2₁/c, a 7.313(4), b 17.156(4), c 7.640(4) 脜, 尾 92.71(5)掳, Z = 4, d_c = 1.454, R = 0.037, R_w = 0.039 for 1040 reflections; 5-Cl-IAA, monoclinic, space group P2₁/c, a 19.141(4), b 5.154(2), c 10.323(3) 脜, 尾 116.23(2)掳, Z = 4, d_c = 1.524, R = 0.039, R_w = 0.042 for 1184 reflections; 6-Cl-IAA, orthorhombic, space group Pbca, a 61.08(1), b 12.115(7), c 7.674(5) 脜, Z = 8 (3 mols./Z), d_c = 1.471, R = 0.052, R_w = 0.052 for 3030 reflections; 7-Cl-IAA, monoclinic, space group P2₁/c, a 20.244(5), b 4.829(2), c 10.728(4) 脜, 尾 116.30(1)掳, Z = 4, d_c = 1.481, R = 0.042, R_w = 0.029 for 889 reflections; 5-Br-IAA, triclinic, space group P1虆, a 5.645(3), b 9.713(4), c 10.019(4) 脜, 伪 116.02(3), 尾 92.67(5), 纬 100.12(4)掳, Z = 2, d_c = 1.754, R = 0.029, R_w = 0.020 for 1865 reflections. At. coordinates are given. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Synthetic Route of C10H8ClNO2).

Liu, Guo-Gui et al. published their research in Tetrahedron in 2012 | CAS: 774-47-0

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Quality Control of 5,6-Difluoroindoline-2,3-dione

Asymmetric cross aldol addition of isatins with 伪,尾-unsaturated ketones catalyzed by a bifunctional Bronsted acid-Bronsted base organocatalyst was written by Liu, Guo-Gui;Zhao, Hua;Lan, Yu-Bao;Wu, Bin;Huang, Xiao-Fei;Chen, Jian;Tao, Jing-Chao;Wang, Xing-Wang. And the article was included in Tetrahedron in 2012.Quality Control of 5,6-Difluoroindoline-2,3-dione This article mentions the following:

The asym. cross-aldol reaction of isatins with 伪,尾-unsaturated ketones has been developed under catalysis by a Cinchona alkaloid-derived bifunctional Bronsted acid-Bronsted base catalyst, affording the aldol adducts in moderate to good yields (18-98%) with moderate to good enantioselectivities (30-97%). The noncovalent organo-catalyzed asym. cross-aldol reaction displays a broad substrate scope and wide functional-group tolerability, albeit the electronic and steric properties of both reaction partners have considerable and regular effects on the reactivity and stereocontrol. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Quality Control of 5,6-Difluoroindoline-2,3-dione).

Liu, Yungen et al. published their research in Chemical Communications (Cambridge, United Kingdom) in 2010 | CAS: 210345-56-5

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) 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. 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: 210345-56-5

[Fe(F₂₀TPP)Cl] catalyzed intramolecular C-N bond formation for alkaloid synthesis using aryl azides as nitrogen source was written by Liu, Yungen;Wei, Jinhu;Che, Chi-Ming. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2010.Recommanded Product: 210345-56-5 This article mentions the following:

The syntheses of alkaloids including indoles, indolines, tetrahydroquinolines, dihydroquinazolinones and quinazolinones were accomplished in moderate to excellent yields via [Fe(F₂₀TPP)Cl] (I) catalyzed intramol. C-N bond formation using aryl azides as nitrogen source. E.g., dihydroquinazolinone derivative II was prepared with 83% yield by refluxing N₃-2-C₆H₄CON(CH₂Ph)₂ with I in (ClCH₂)₂. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5Recommanded Product: 210345-56-5).

Basak, Shyam et al. published their research in ACS Catalysis in 2020 | CAS: 4583-55-5

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. 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.Formula: C10H10BrN

B(C₆F₅)₃-Catalyzed Direct C3 Alkylation of Indoles and Oxindoles was written by Basak, Shyam;Alvarez-Montoya, Ana;Winfrey, Laura;Melen, Rebecca L.;Morrill, Louis C.;Pulis, Alexander P.. And the article was included in ACS Catalysis in 2020.Formula: C10H10BrN This article mentions the following:

A new approach to the direct C3-alkylation of indoles and oxindoles using a B(C₆F₅)₃ catalyst and amine-derived alkylating agents to give arylated indole derivatives I [R = H, Me, n-hexyl, Bn; R¹ = H, Me, Ph; R² = H, 4-Me, 5-Cl, etc.; R³ = Me, Et, Bn, etc.] and oxindole derivatives II [R⁴ = H, 5-F, 6-Me, etc.; R⁵ = CO₂Et, Ph, 4-MeC₆H₄, etc.] were reported. Also this borane-catalyzed strategy in alkylation-ring opening cascade process to afford functionalized indoles III [R₆ = H, Me; R⁷ = H, Me; R⁸ = H, 5-OMe; R⁹ = 2,4,6-(Me)₃C₆H₂, 2-MeOC₆H₄, 2-Me-4-MeOC₆H₃, 2,6-(Me)₂-4-MeOC₆H₂] was reported. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Formula: C10H10BrN).

Chen, Lingfeng et al. published their research in European Journal of Medicinal Chemistry in 2017 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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.Category: indole-building-block

Structure-based design and synthesis of 2,4-diaminopyrimidines as EGFR L858R/T790M selective inhibitors for NSCLC was written by Chen, Lingfeng;Fu, Weitao;Feng, Chen;Qu, Rong;Tong, Linjiang;Zheng, Lulu;Fang, Bo;Qiu, Yinda;Hu, Jie;Cai, Yuepiao;Feng, Jianpeng;Xie, Hua;Ding, Jian;Liu, Zhiguo;Liang, Guang. And the article was included in European Journal of Medicinal Chemistry in 2017.Category: indole-building-block This article mentions the following:

Mutated epidermal growth factor receptor (EGFR) is a major driver of non-small cell lung cancer (NSCLC). The EGFRT790M secondary mutation has become a leading cause of clin.-acquired resistance to gefitinib and erlotinib. Herein, structure-based design approach to increase the potency and selectivity of the previously reported reversible EGFR inhibitor I, at the kinase and cellular levels has been reported. Three-step structure-activity relationship exploration led to promising compounds II (R¹ = Br; R² = 1-methyl-1H-indol-6-yl, 2,3-dihydro-1H-inden-5-yl; R³ = OMe; R⁴ = 4-methyl-1-piperazinyl) with unique chem. structure and binding mode from the other third-generation tyrosine kinase inhibitors. In a human NSCLC xenograft model, the above compounds exhibited dose-dependent tumor growth suppression without toxicity. These selective inhibitors are promising drug candidates for EGFRT790M-driven NSCLC. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Category: indole-building-block).

Lv, Mei-fang et al. published their research in Asian Journal of Organic Chemistry in 2015 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.COA of Formula: C8H6N2O2

Catalyst-Free Chemoselective Reduction of Nitroarenes Using Thiourea as a Hydrogen Source was written by Lv, Mei-fang;Lu, Guo-ping;Cai, Chun. And the article was included in Asian Journal of Organic Chemistry in 2015.COA of Formula: C8H6N2O2 This article mentions the following:

A newly developed protocol for the reduction of nitroarenes using thiourea as the hydrogen source was described. The method was simple, inexpensive and easily applicable to the preparation of a variety of substituted anilines with high yields and selectivity. In contrast to traditional hydrogenation methods, this chem. does not required a catalyst, elaborated work-up procedures, or the use of high-pressure equipment. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4COA of Formula: C8H6N2O2).

Schulte, K. E. et al. published their research in Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft in 1955 | CAS: 6639-06-1

3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Safety of 3-(1H-Indol-1-yl)propanoic acid

Reactions of unsaturated bromocarbonyl compounds with primary amines. II. The preparation of 1,2,5-substituted pyrroles was written by Schulte, K. E.;Zinnert, F.. And the article was included in Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft in 1955.Safety of 3-(1H-Indol-1-yl)propanoic acid This article mentions the following:

Condensation of AcH and PhAc (Dubois C.A. 43, 6159i) gave crotonophenone, b₈ 122掳, which brominated in HOAc gave 2,3-dibromobutyrophenone, m. 93-4掳. Reaction with N-bromosuccinimide gave the same dibromo derivative and an impure oily product, presumably 4-bromocrotonophenone, which on condensation-with BuNH₂ gave an impure product (no anal.), presumably 1-butyl-2-phenylpyrrole, absorption maximum at 2210 A. Friedel-Crafts reaction of benzene and 2-hexenoyl chloride gave 54.6% 2-hexenophenone (I); semicarbazide, m. 162.5-3.5掳. Bromination of I in HOAc and recrystallization from MeOH gave 2,3-dibromohexanophenone, m. 59.5-60.5掳. Bromination of 3.5 g. I in 20 cc. CCl₄ with 3.6 g. N-bromosuccinimide and 25 mg. Bz₂O₂ under reflux gave 4.5 g. oil, presumably 4-bromo-2-hexenophenone. A solution of 2.6 g. of this product in 40 cc. petr. ether and 5 g. BuNH₂ in 20 cc. 50% EtOH shaken 5 min., dried with Na₂SO₄ and the solution fractionally distilled gave 0.9 g. of a viscous oil analyzing correctly for 1-butyl-2-ethyl-5-phenylpyrrole, b₈ 148-9掳, absorption maximum 2210 A. Et crotonate (14.8 g.) refluxed 4 h. with 23 g. N-bromosuccinimide and 100 mg. Bz₂O₂, cooled, filtered and the solution fractionally distilled gave 60% Et 4-bromocrotonate, b₁₅ 80-81掳. Et 2-hexenoate, b₁₈ 73-4掳, and Et 2-decenoate, b₂₀ 138.5-5掳, were prepared in 81.5 and 76.1% yield, resp., from the acids via the acid chlorides. Bromination of these esters with N-bromosuccinimide gave 64%-Et 4-bromo-2-hexenoate, b₁₈ 119-21掳, and 53.5% Et 4-bromo-2-decenoate, b₁₅ 162-4掳. Neither these esters or Et 4-bromocrotonate gave pyrrole derivatives on reaction with aniline or with BuNH₂. 2-Penten-4-one, 3-hexen-2-one, 2-methyl-2-methyl-2-penten-4-one, 3-undecen-2-one, and 2-methyl-2-pentenal gave no pure bromo derivatives on reaction with N-bromosuccinimide. In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1Safety of 3-(1H-Indol-1-yl)propanoic acid).

Lin, Hui-Shan et al. published their research in Chemical Communications (Cambridge, United Kingdom) in 2022 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 5-Chloroindole-3-carboxaldehyde

Electrosynthesis of (hetero)aryl nitriles from 伪-imino-oxy acids via oxidative decarboxylation/N-O cleavage was written by Lin, Hui-Shan;Chen, Shu-Jun;Huang, Jing-Mei. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2022.Recommanded Product: 5-Chloroindole-3-carboxaldehyde This article mentions the following:

A new method for the synthesis of (hetero)aryl nitriles via iminyl radicals was developed through the electrochem. oxidative decarboxylation of 伪-imino-oxy acids. This protocol provides an efficient approach to nitriles with a broad range of functional-group tolerance under ambient conditions and can be applied for one-pot gram-scale synthesis. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Recommanded Product: 5-Chloroindole-3-carboxaldehyde).