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Letters in Organic Chemistry

Author(s): Abdullah K. Jarrar, Mustafa M. El-Abadelah*, Salim S. Sabri, Jalal A. Zahra* and Mohammad S. Hamdan

DOI: 10.2174/1570178619666220314151114

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Thiophene Ring-Opening Reactions V. Expedient Synthesis of 1,3,4- Thiadiazoline-Sulfanyl[1,3]thiazin-4-one Hybrids

Page: [976 - 982] Pages: 7

  • * (Excluding Mailing and Handling)

Abstract

The preparation of 6-chloro-5-nitrothieno[3,2-e][1,3]thiazin-4-one incorporating 2-(Nmorpholinyl) moiety is achieved via a conventional route. Interaction of the latter substrate with a set of N'-(aryl) benzothiohydrazides 1a-f, in the presence of triethylamine, led to a thiophene ring-opening process with the consequent generation of the respective thiolate salts 8a-f. Alkylation of the latter, using methyl iodide or allyl chloride, generated the respective novel 1,3,4-thiadiazoline–6-sulfanyl-1,3- thiazin-4-one hybrids, the structures of which were verified by HRMS and NMR spectral data.

Keywords: N'-(Aryl)benzothiohydrazides, chalcogen bond, formal [4+1] annulation, thieno[3, 2-e][1, 3]thiazin-4-one, S-allylation, β-nitrothiophenes.

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