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Regio- and stereoselective synthesis of spiro[1-benzothiepine-4(5h), 3′(3h)-pyrazol]-5-ones

✍ Scribed by Nawal Mishriky; Adel S. Girgis; Hanaa M. Hosni; Hanaa Farag

Publisher: Journal of Heterocyclic Chemistry
Year: 2006
Tongue: English
Weight: 466 KB
Volume: 43
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570430618

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✦ Synopsis

Abstract

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Reaction of (4__E__)‐4‐arylmethylene‐3,4‐dihydro‐1‐benzothiepin‐5(2__H__)‐ones 3a‐e with nitrilimines (generated in situ via triethylamine dehydrohalogenation of the corresponding hydrazonoyl chlorides 4a, b) in refluxing benzene, afforded 2′,4′,5′‐triaryl‐2,2′,3,4′‐tetrahydro‐spiro[1‐benzothiepine‐4(5__H__),3′(3__H__)‐pyrazol]‐5‐ones 5a‐i and not the isomeric forms spiro[1‐benzothiepine‐4(5__H__),4′(4__H__)‐pyrazol]‐5‐ones 6 in high regioselective manner. Single crystal X‐ray diffraction studies of 5a, f, g indicated that the isolated products are 3′R, 4′ S.

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