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2000
Volume 22, Issue 5
  • ISSN: 1570-1794
  • E-ISSN: 1875-6271

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 formed electrophilic -alkoxycarbonylbenzimidazolium reagents. For the first time, their application for -alkylation of the indole nitrogen atom is announced toward novel tris-heterocyclic 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 method has been successfully applied, using an -amidoalkylation reaction of indoles with ,-diacyliminium reagents derived from benzimidazoles and alkyl chloroformates.

Results

The reactions led to the obtaining of ten novel compounds (, ), 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 (, ) through the reaction of -alkylation of the indole nitrogen atom is announced giving another potential synthetic application of the ,-dialkoxycarbonyl-5,6-dimethylbenzimidazolium adducts.

Conclusion

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

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2025-01-20
2025-08-14

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A Convenient one-pot Approach to the Synthesis of Novel Benzimidazole-Indole Molecular Hybrids as Benzazacamalexin Related Analogues
Curr. Org. Synth. 22, 631 (2025); https://doi.org/10.2174/0115701794364219241228094932
/content/journals/cos/10.2174/0115701794364219241228094932
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  • Article Type:     Research Article
Keyword(s): azacamalexin; benzimidazole; benzocamalexin; Camalexin; in situ reactions; indole; N-acylbenzimidazolium ions; tris-heterocycles

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