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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Thiophene Ring-Opening Reactions IV. Facile Generation of Novel Ethyl 4-hydroxy-6-thioxonicotinate-1,3,4-thiadiazoline Hybrids

Author(s): Mohammed M. Abadleh, Ahmad H. Abdullah, Jalal A. Zahra*, Salim S. Sabri, Firas F. Awwadi and Mustafa M. El-Abadelah*

Volume 19, Issue 6, 2022

Published on: 13 January, 2022

Page: [504 - 510] Pages: 7

DOI: 10.2174/1570178618666211110141423

Price: $65

Abstract

A set of triethylammonium 4-oxo-6-pyridinethiolate–1,3,4-thiadiazoline hybrids (3a-e) were prepared via the reaction of ethyl 2-chloro-6-cyclopropyl-3- nitro-4-oxothieno[2,3-b]pyridine- 5-carboxylate (2) with the appropriate thiobenzoyl- hydrazide (1a-e) in acetonitrile and triethylamine. These hybrids were readily converted, under neutral mild conditions, into the corresponding 4-hydroxy-6-thioxopyridine –thiadiazoline hybrids (5a-e). The structures of the latter set are supported by HRMS, 1H NMR, and 13C NMR spectral data and further confirmed by single-crystal Xray diffraction studies. Alkylation of these hybrids in the presence of triethylamine occurred exclusively at the 6-thioxosulfur, yielding the respective 6-sulfanyl derivatives (6a-c).

Keywords: N'-(Aryl)benzothiohydrazides, 4-oxothieno[2, 3-b]pyridine, formal [4 + 1] annulation, 4-hydroxy-6-thioxonicotinate, regioselective S-alkylation, hybrids.

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