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The reaction of acetic acid 2-selenoxo-2H-pyridin-1-yl esters with benzynes: A convenient route to Benzo[b]seleno[2,3-b]pyridines

✍ Scribed by U. Narasimha Rao; Ramadas Sathunuru; John. A. Maguire; Ed Biehl

Publisher: Journal of Heterocyclic Chemistry
Year: 2004
Tongue: English
Weight: 288 KB
Volume: 41
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570410103

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✦ Synopsis

Abstract

Benzyne and its 3,4,5,6‐tetraphenyl, 3‐ and 4‐methyl, 3‐methoxy and 4,5‐difluoro derivatives react with acetic acid 2‐selenoxo‐2__H__‐pyridin‐1‐yl esters 4a‐e to give benzo[b]seleno[2,3‐b]pyridines 10–15 in modest yields. The benzynes were generated by one or more of the following methods: diazotization of anthranilic acids 5a‐g with isoamyl nitrate; mild thermal decomposition of 2‐diazoniobenzenecarboxylate hydrochlorides 6a‐d treatment of (phenyl)[o‐(trimethylsilyl)phenyl]iodonium triflate (7) with tetrabutylammonium fluoride; and treatment of 2‐trimethylsilylphenyl triflates 8a‐c with cesium fluoride. In all the reactions, the corresponding 2‐(methylselenenyl)pyridines 16a‐d were also obtained suggesting that these reactions may involve selenium addition to benzyne via a SET (single electron transfer).

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