Tag: 162.15

Convenient synthesis of chiral tryptophan derivatives using Negishi cross-coupling was written by Tanaka, Minoru;Hikawa, Hidemasa;Yokoyama, Yuusaku. And the article was included in Tetrahedron in 2011.Category: indole-building-block This article mentions the following:

A facile synthetic procedure for chiral tryptophan derivatives using Negishi cross-coupling reaction of serine-derived iodoalanine with 3-haloindole is described. The best result was obtained when the reaction of N-tosyl-3-bromoindole with N-Cbz-iodoalanine Me ester (Cbz = benzyloxycarbonyl) was carried out by the combination of Pd₂(dba)₃ and sterically hindered ferrocenyl ligand Q-PHOS. This reaction condition not only gave the desired tryptophan derivative as high as 76% yield, but also suppressed the formation of undesired products, the dehalogenated indole and the homodimer of indole, which were difficult to sep. This reaction was extended to the synthesis of various tryptophan derivatives having substituents on the benzene ring. The characteristic of this reaction is the practical biomimetic synthesis of chiral tryptophan derivatives in one-step. In the experiment, the researchers used many compounds, for example, 4-Nitroindole (cas: 4769-97-5Category: indole-building-block).

4-Nitroindole (cas: 4769-97-5) 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.Category: indole-building-block

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

High Proportion of Chiral Crystallization of Achiral Indolyl Sulfonamides: Effect of Intermolecular Interactions was written by Kikkawa, Shoko;Maeno, Isae;Katagiri, Kosuke;Murayama, Yuta;Nozawa, Mariko;Hikawa, Hidemasa;Azumaya, Isao. And the article was included in Crystal Growth & Design in 2021.Product Details of 4769-97-5 This article mentions the following:

We investigated the effect of indole moieties on chiral crystallization In this regard, we assessed the influence of intermol. interactions and contacts on the assembly of these mols. A systematic anal. of 62 crystal structures of secondary aromatic sulfonamides bearing 4-, 5-, 6-, and 7-aminoindolyl groups revealed that the proportion of indolyl compounds showing chiral crystallization was apparently higher (21%, except for crypto-racemate) than that of nonindolyl sulfonamides (11%). Moreover, 33% (5 out of 15 crystals) and 44% (7 out of 16 crystals) of 4- and 7-indolyl sulfonamide derivatives preferred chiral crystallization, resp. This suggested a correlation between the type of contact and the chirality of the assembly of adjacent mols. Specifically, the proportion of achiral indolyl sulfonamides undergoing chiral crystallization was drastically increased by N(indole)H···O interactions, slightly increased by C(sp²)H···π interactions, and decreased owing to π···π interactions. These tendencies were also true for sulfonamides with different substituents, which suggested that the T-shape contact would be more favorable than π···π interactions for chiral crystallization In the experiment, the researchers used many compounds, for example, 4-Nitroindole (cas: 4769-97-5Product Details of 4769-97-5).

4-Nitroindole (cas: 4769-97-5) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Product Details of 4769-97-5

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