Synthesis of nitrogen-containing heterocyclic compounds was written by de Stevens, George;Dughi, Marylou;Lukaszewski, Halina;Blatter, Herbert. And the article was included in Oesterreichische Chemiker-Zeitung in 1962.HPLC of Formula: 90271-86-6 This article mentions the following:
A new heterocyclic compound, 1,2,4,5-tetrahydro-3-methyl-1,3-benzodiazepine (I, R = H2), pKa < 2, was synthesized from o-aminophenylacetic acid methylamide (II) and formaldehyde through I (R = O). Condensation of II with BzH in boiling diethylene glycol dimethyl ether produced only 3-benzylideneoxindole; however, a quant. yield of o-MeNHCOCH2C6H4N:CHPh, λ 260 mμ (ε 15.760), and 320 mμ (ε 6450), was obtained by carrying out the condensation at 95°. New tetracyclic indoles were synthesized from 1-carbethoxymethyl-1,2,3,4-tetrahydro-β-carboline (III, R = EtO), which reacted with MeNH2 to give a good yield of III (R = NHMe) (IV). IV condensed with formaldehyde in boiling ethanol gave 68% 3-methylaza-1,2,3,4,6,7,12,12boctahydro-2-oxoindolo[2,3-a]pyridocoline (V, R = Me). Condensation of IV with appropriate benzaldehyde gave V (R = Ph, p-ClC6H4, 3,4,5-(MeO)3C6H2, and p-MeOC6H4). Reduction of the cyclic amides with LiAlH4 resulted in loss of carbonyl group. Reduction of IV with LiAlH4 gave the corresponding amino alcohol (VI), which with HCHO gave VII. Replacement of formaldehyde with benzaldehyde did not produce the expected oxazine but the dimeric compound (VIII). Condensation of indole-3-carboxaldehyde with nitropropane in presence of (NH4)2HPO4, AcOH, and Ac2O resulted in 3-cyanoindole, 60%, m. 178°. This method was extended to other aromatic aldehydes to give: 5-bromo-3-cyanoindole, 41%; 3-cyano-7-azaindole, 40%; p-dimethylaminobenzonitrile, 77%; p-chlorobenzonitrile, 50%; 3,4,5-trimethoxybenzonitrile, 74%; p-isopropylbenzonitrile, 30%. 20 references. In the experiment, the researchers used many compounds, for example, 5-Bromo-3-cyanoindole (cas: 90271-86-6HPLC of Formula: 90271-86-6).
5-Bromo-3-cyanoindole (cas: 90271-86-6) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.HPLC of Formula: 90271-86-6
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