Title:Thiophene Ring-Opening Reactions V. Expedient Synthesis of 1,3,4-
Thiadiazoline-Sulfanyl[1,3]thiazin-4-one Hybrids
Volume: 19
Issue: 11
Author(s): Abdullah K. Jarrar, Mustafa M. El-Abadelah*, Salim S. Sabri, Jalal A. Zahra*Mohammad S. Hamdan
Affiliation:
- Department of Chemistry, Faculty of Science, The University of Jordan, Amman 11942, Jodran
- Department of Chemistry, Faculty of Science, The University of Jordan, Amman 11942, Jodran
Keywords:
N'-(Aryl)benzothiohydrazides, chalcogen bond, formal [4+1] annulation, thieno[3, 2-e][1, 3]thiazin-4-one, S-allylation, β-nitrothiophenes.
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.
