A Convenient one-pot Approach to the Synthesis of Novel Benzimidazole-Indole Molecular Hybrids as Benzazacamalexin Related Analogues.

IF 1.7 4区化学 Q3 CHEMISTRY, ORGANIC

Current organic synthesis Pub Date : 2025-02-07 DOI:10.2174/0115701794364219241228094932

Yordan Stremski, Maria Bachvarova, Desislava Kirkova, Elena Milinova, Stela Statkova-Abeghe

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引用次数: 0

Abstract

Background: New benzazacamalexin-related analogues are synthesized in an easily accessible one-pot approach. The method is based on the reaction of indoles with in situ formed electrophilic N-alkoxycarbonylbenzimidazolium reagents. For the first time, their application for N-alkylation of the indole nitrogen atom is announced toward novel tris-heterocyclic hybrids. The structure of newly obtained products was spectrally charac-terized by 1D and 2D-NMR, FTIR and HRMS spectral data. The current scientific re-search is based on the application of a convenient and efficient route for the preparation of various benzimidazoles. This approach is both straightforward and economical, utilizing readily accessible and affordable reagents leading to target compounds.

Objective: The synthesis of novel benzimidazole-indole molecular hybrids as benzazaca-malexin related analogues.

Methods: A suitable in situ method has been successfully applied, using an α-amidoalkylation reaction of indoles with N,N-diacyliminium reagents derived from ben-zimidazoles and alkyl chloroformates.

Results: The reactions led to the obtaining of ten novel compounds (5a-e, 6a-e), including bromine and iodine-containing benzo-analogues on a gram-scale scope and yields ranging from 82% to 99%. For the first time the synthesis of indole tris-heterocycles (7a, b) through the reaction of N-alkylation of the indole nitrogen atom is announced giving an-other potential synthetic application of the N,N-dialkoxycarbonyl-5,6-dimethylbenzimidazolium adducts.

Conclusion: The structure of the newly synthesized products is spectrally analysed and proved.

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来源期刊

Current organic synthesis 化学-有机化学

CiteScore

3.40

自引率

5.60%

发文量

审稿时长

6-12 weeks

期刊介绍： Current Organic Synthesis publishes in-depth reviews, original research articles and letter/short communications on all areas of synthetic organic chemistry i.e. asymmetric synthesis, organometallic chemistry, novel synthetic approaches to complex organic molecules, carbohydrates, polymers, protein chemistry, DNA chemistry, supramolecular chemistry, molecular recognition and new synthetic methods in organic chemistry. The frontier reviews provide the current state of knowledge in these fields and are written by experts who are internationally known for their eminent research contributions. The journal is essential reading to all synthetic organic chemists. Current Organic Synthesis should prove to be of great interest to synthetic chemists in academia and industry who wish to keep abreast with recent developments in key fields of organic synthesis.