NaH promoted [4+3] annulation of crotonate-derived sulfur ylides with thioaurones: synthesis of 2,5-dihydrobenzo[4,5]thieno[3,2-b]oxepines

The [4+3] annulation reaction of crotonate-derived sulfur ylides with thioaurones has, for the first time, been reported using NaH as the base. A diverse array of 2,5-dihydrobenzo[4,5]thieno[3,2-b]oxepines is obtained in good to excellent yields. The proposed mechanism is investigated and supported...

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Published in:Chemical communications (Cambridge, England) England), 2017-09, Vol.53 (77), p.10672-10675
Main Authors: Zhang, Youquan, Yu, Aimin, Jia, Jiru, Ma, Shanshan, Li, Ke, Wei, Yin, Meng, Xiangtai
Format: Article
Language:English
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Summary:The [4+3] annulation reaction of crotonate-derived sulfur ylides with thioaurones has, for the first time, been reported using NaH as the base. A diverse array of 2,5-dihydrobenzo[4,5]thieno[3,2-b]oxepines is obtained in good to excellent yields. The proposed mechanism is investigated and supported by DFT calculations.
ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc04466f