Published in

Springer, Monatshefte für Chemie - Chemical Monthly, 11(152), p. 1377-1387, 2021

DOI: 10.1007/s00706-021-02850-3

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Unexpected ring-opening of 2,3-dihydropyridines

This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

AbstractThe reaction of 2,3-dihydropyridines with sulfonyl halides surprisingly yielded open chain dienes with sulfonylimine structure. The products were specific out of several possible isomers and, therefore, a separation of isomers was not necessary. All new compounds were characterized using FT-IR spectroscopy, HRMS, and NMR spectroscopy. A bicyclic by-product from the reaction of a 2,3-dihydropyridine with mesyl chloride was isolated and its structure elucidated using a single X-ray crystal analysis. Some biological activities, like antimicrobial and cytotoxic properties were investigated. Graphic abstract