Issue 34, 2015

Efficient strategy for construction of 6-carbamoylfulvene-6-carboxylate skeletons via [3 + 2] cycloaddition of 1-cyanocyclopropane 1-ester with β-nitrostyrenes

Abstract

An efficient and straightforward synthetic protocol has been developed for the preparation of 6-carbamoylfulvene-6-carboxylates via a cycloaddition reaction between 1-cyanocyclopropane 1-esters and β-nitrostyrenes for the generation of a wide range of structurally interesting and pharmacologically significant compounds. The reaction utilises Et3N promoted C–C bond cleavage, two new C–C bond formations of 1-cyanocyclopropane 1-ester with β-nitrostyrene and simultaneous conversion of a cyano group into amide in a domino fashion.

Graphical abstract: Efficient strategy for construction of 6-carbamoylfulvene-6-carboxylate skeletons via [3 + 2] cycloaddition of 1-cyanocyclopropane 1-ester with β-nitrostyrenes

Supplementary files

Article information

Article type
Communication
Submitted
15 Feb 2015
Accepted
10 Mar 2015
First published
16 Mar 2015

RSC Adv., 2015,5, 26491-26495

Author version available

Efficient strategy for construction of 6-carbamoylfulvene-6-carboxylate skeletons via [3 + 2] cycloaddition of 1-cyanocyclopropane 1-ester with β-nitrostyrenes

C. Tan, W. Ye, J. Yao, J. Liu, S. Xue, Y. Li and C. Wang, RSC Adv., 2015, 5, 26491 DOI: 10.1039/C5RA02918J

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