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

IF 2.5 4区化学 Q3 CHEMISTRY, ORGANIC

Current organic synthesis Pub Date : 2025-01-01 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 trisheterocyclic hybrids. The structure of newly obtained products was spectrally characterized by 1D and 2D-NMR, FTIR and HRMS spectral data. The current scientific research 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 benzazacamalexin 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 benzimidazoles 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 another 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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一锅法合成新型苯并咪唑-吲哚分子杂合体苯并扎卡霉素相关类似物。

背景：新的苯扎卡霉素相关的类似物是在一个容易获得的一锅方法合成。该方法是基于吲哚与原位形成的亲电性n -烷氧羰基苯并咪唑试剂的反应。首次报道了它们在吲哚氮原子n -烷基化上的应用，形成了新的三杂环杂化物。通过1D和2d nmr、FTIR和HRMS光谱数据对新产物的结构进行了表征。目前的科学研究是基于应用一种方便、高效的路线来制备各种苯并咪唑。这种方法既直接又经济，利用容易获得和负担得起的试剂导致目标化合物。目的：合成新型苯并咪唑-吲哚类分子杂合体，作为苯扎卡-马甲新相关类似物。方法：采用原位法，将吲哚与苯并咪唑衍生的N，N-二酰基胺试剂和氯甲酸烷基酯进行α-氨基烷基化反应。结果：反应得到10个新化合物（5a-e, 6a-e），包括含溴和含碘的苯并类似物，产率在82% ~ 99%之间。首次通过吲哚氮原子的N-烷基化反应合成了吲哚三杂环（7a, b），为N，N-二氧羰基-5,6-二甲基苯并咪唑加合物提供了另一种潜在的合成应用。结论：对新合成产物的结构进行了光谱分析和验证。

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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.