Synthesis of 9-Substituted Imidazo[1,2-a]benzimidazoles Containing a 5-Nitrofuran-2-yl Fragment
- Authors: Kuzmenko T.A.1, Divaeva L.N.1, Sayapin Y.A.2, Morkovnik A.S.1, Borodkin G.S.1
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Affiliations:
- Research Institute of Physical and Organic Chemistry
- Southern Scientific Center
- Issue: Vol 55, No 10 (2019)
- Pages: 1547-1553
- Section: Article
- URL: https://journals.rcsi.science/1070-4280/article/view/221271
- DOI: https://doi.org/10.1134/S1070428019100130
- ID: 221271
Cite item
Abstract
9-Substituted 2-(5-nitrofuran-2-yl)-9H-imidazo[1,2-a]benzimidazoles were synthesized for the first time by cyclization of quaternary salts obtained from 1-substituted benzimidazol-2-amines and 2-bromo-1-(5-nitrofuran-2-yl)ethan-1-one. 9-R-2-Methyl(aryl)-9H-imidazo[1,2-a]benzimidazoles reacted with 5-nitrofuran-2-carbaldehyde and 4-nitrobenzaldehyde to give the corresponding secondary alcohols as a result of aldehyde addition to the 3-position of the tricyclic system. The Witting olefination of ethyl 2-(bromomethyl)-9-methyl-9H-imidazo[1,2-a]benzimidazole-3-carboxylate afforded 2-ethenylimidazo[1,2-a]benzimidazoles.
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About the authors
T. A. Kuzmenko
Research Institute of Physical and Organic Chemistry
Email: asmork2@ipoc.rsu.ru
Russian Federation, Rostov-on-Don
L. N. Divaeva
Research Institute of Physical and Organic Chemistry
Email: asmork2@ipoc.rsu.ru
Russian Federation, Rostov-on-Don
Yu. A. Sayapin
Southern Scientific Center
Email: asmork2@ipoc.rsu.ru
Russian Federation, Rostov-on-Don
A. S. Morkovnik
Research Institute of Physical and Organic Chemistry
Author for correspondence.
Email: asmork2@ipoc.rsu.ru
Russian Federation, Rostov-on-Don
G. S. Borodkin
Research Institute of Physical and Organic Chemistry
Email: asmork2@ipoc.rsu.ru
Russian Federation, Rostov-on-Don
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