Synthesis of new spiro-[isothiochromene-3,5′-isoxazolidin]-4(1H)-ones
✍ Scribed by Brahim Bennani; Bouchra Filali Baba; Najib Ben Larbi; Abdelatif Boukir; Abdelali Kerbal; Mostafa Mimouni; Taibi Ben Hadda; Bartosz Trzaskowski; Abraham F. Jalbout
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 2007
- Tongue
- English
- Weight
- 401 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
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A series of seven new 2′,3′,4′‐substituted spiro[isothiochromene‐3,5′‐isoxazolidin]‐4(1__H__)‐ones (7‐13) has been prepared in the reaction of benzylidene(phenyl)azane oxide (5) or benzylidene(methyl)azane oxide (6) with (3Z)‐3‐(4‐substituted‐benzylidene)‐1__H__‐isothio‐ chromen‐4(3__H__)‐one (1‐4). The reaction occurs by a 1,3‐dipolar cycloaddition mechanism that leads to the regiospecific formation of various spiroisoxazolidines (7‐13).
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## Abstract magnified image 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
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