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Org Biomol Chem. 2014 Aug 28;12(32):6114-20. doi: 10.1039/c4ob00996g. Epub 2014 Jul 2.

Copper-catalyzed annulation of heteroaromatic β-halo-α,β-unsaturated carboxylic acids with alkynes for the synthesis of indolo[2,3-c]pyrane-1-ones and thieno[2,3-c]pyrane-7-ones.

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1
Shanghai Center for Systems Biomedicine, Ministry of Education Key Laboratory of Systems Biomedicine, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China. xunxiang_guo@sjtu.edu.cn.

Abstract

The annulation of heteroaromatic β-halo-α,β-unsaturated carboxylic acids with alkynes proceeds efficiently in the presence of Cu(OAc)2·H2O as a catalyst to afford the corresponding indolo[2,3-c]pyrane-1-ones and thieno[2,3-c]pyrane-7-ones in moderate to good yields. This strategy offers a simple and efficient route for the synthesis of indolo[2,3-c]pyrane-1-ones and thieno[2,3-c]pyrane-7-ones with good tolerance to a variety of functional groups from easily available heteroaromatic β-halo-α,β-unsaturated carboxylic acids.

PMID:
24987834
DOI:
10.1039/c4ob00996g
[Indexed for MEDLINE]
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