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Issue 37, 2017
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DBU-mediated [4 + 1] annulations of donor–acceptor cyclopropanes with carbon disulfide or thiourea for synthesis of 2-aminothiophene-3-carboxylates

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Abstract

DBU-mediated [4 + 1] annulations of donor–acceptor cyclopropanes with carbon disulfide or thiourea to form 2-aminothiophene-3-carboxylate derivatives have been discovered. This reaction proceeds via the ring opening of donor–acceptor cyclopropanes to produce a 2-(iminomethylene)but-3-enoate intermediate, followed by the attack of an S-nucleophile for regioselective intermolecular nucleophilic addition, intramolecular S-nucleophilic addition, and final aromatization. A variety of functional groups could be tolerated under the reaction conditions.

Graphical abstract: DBU-mediated [4 + 1] annulations of donor–acceptor cyclopropanes with carbon disulfide or thiourea for synthesis of 2-aminothiophene-3-carboxylates

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Supplementary files

Article information


Submitted
29 Jul 2017
Accepted
01 Sep 2017
First published
01 Sep 2017

Org. Biomol. Chem., 2017,15, 7878-7886
Article type
Paper

DBU-mediated [4 + 1] annulations of donor–acceptor cyclopropanes with carbon disulfide or thiourea for synthesis of 2-aminothiophene-3-carboxylates

Z. Su, S. Qian, S. Xue and C. Wang, Org. Biomol. Chem., 2017, 15, 7878
DOI: 10.1039/C7OB01886J

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