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Reaction of 3-Cl/OMe-Substituted 5-Nitrobenzisothiazoles with Hydrazine: Structural and Computational Evidence for Rearrangement Pathways Implicating Intramolecular Formation of Pivotal Meisenheimer Complexes by Zheng Sonia Lin; Xing Tong; Brian Patrick; Pierre Kennepohl; David S. Grierson is a Chemistry article available to read on EtoBox.

What is Reaction of 3-Cl/OMe-Substituted 5-Nitrobenzisothiazoles with Hydrazine: Structural and Computational Evidence for Rearrangement Pathways Implicating Intramolecular Formation of Pivotal Meisenheimer Complexes about?

In projected structure-activity relationship studies of the novel diheteroarylamide-based anti-HIV agent (1C8), one objective was to evaluate the influence of incorporating the central amide motif in into a five-membered pyrazolone ring, as found in . It was envisaged that compound could be prepared through reaction of 3-hydrazino-5-nitrobenzisothiazole with the methyl ester of 4-chloropyridine-3-carboxylic acid, followed by N-methylation of the pyridine nitrogen. However, the reaction of 3-methoxyl-5-nitrobenzisothiazole with hydrazine resulted in formation of ring-opened hydrazonate product . In the corresponding reaction with 3-chloro-5-nitrobenzisothiazole, a different rearrangement product was formed, in which two 2,1-benzisothiazole units are joined by a sulfur bridge. Meisenheimer complex formation, favored by the presence of the 5-nitro substituent on the benzisothiazole ring, was postulated to be a key feature in the formation of these deep-seated rearrangement products. Support for the proposed formation of the pivotal Meisenheimer complexes and their subsequent evolution to the observed products in which the benzisothiazole sulfur atom is either expelled or maintained in

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Author

Zheng Sonia Lin; Xing Tong; Brian Patrick; Pierre Kennepohl; David S. Grierson

Publisher

American Chemical Society (ACS)

Published

2021

Language

EN

Field

Chemistry (Physical Sciences)