Copper-Catalyzed Ultrasonic-Promoted Coupling of Acetylene Analogs,
Dialkyl azo dicarboxylate, and Benzazoles to Assemble Tricyclic Fused-
Ring [1,2,3]triazolo[3,4-b][1,3]benzazole Analogs

Manijeh       Nematpour; Nafiseh       Karimi; Mohammad       Mahboubi-Rabbani

doi:10.2174/1570178618666211001120336

Abstract

An unprecedented copper-catalyzed reaction of acetylene analogs with dialkyl azo dicarboxylate and benzazole analogs via a cross-coupling sequence was reported. A library of triazolobenzazole fused ring systems including [1,2,3] triazolo [3,4-b] [1,3] benzothiazole, [1,2,3] triazolo [3,4-b] [1,3] benzoxazole and [1,2,3] triazolo[3,4-b][1,3]benzimidazole structures were obtained in moderate to excellent yields under very mild reaction conditions. Structural confirmation of the final products became possible using different methods like spectroscopy and elemental analysis. The control experiments indicated C-H activation of acetylene by copper salts, followed by cycloaddition between a 2-(phenylethynyl)benzo[d]azol-3(2H)-yl anion and azo dicarboxylate as the key mechanistic feature. The broad substrate scope with simple and easily affordable starting materials, as well as mild reaction conditions are the noticeable attributes of this methodology, which provides facile access to the desired products.

Keywords: Cu-catalyzed, triazolobenzazoles, azo dicarboxylate, terminal alkyne, ultrasonication.

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DOI https://dx.doi.org/10.2174/1570178618666211001120336	Print ISSN 1570-1786
Publisher Name Bentham Science Publisher	Online ISSN 1875-6255

Letters in Organic Chemistry

Copper-Catalyzed Ultrasonic-Promoted Coupling of Acetylene Analogs, Dialkyl azo dicarboxylate, and Benzazoles to Assemble Tricyclic Fused- Ring [1,2,3]triazolo[3,4-b][1,3]benzazole Analogs

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