1,3-Dipolar cycloadditions of 2-thio-3-chloroacrylamides with diazoalkanes

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1,3-Dipolar cycloadditions of 2-thio-3-chloroacrylamides with diazoalkanes

Kissane, Marie; Lawrence, Simon E.; Maguire, Anita R.
Date: 2010-06-21
Copyright: ©2010, The Authors. Exclusive licence to publish RSC Publishing.
Related: http://pubs.rsc.org/en/content/articlelanding/2010/ob/c002479a
http://www.rsc.org/suppdata/ob/c0/c002479a/c002479a.txt
http://www.rsc.org/suppdata/ob/c0/c002479a/c002479a.pdf
Citation: KISSANE, M., LAWRENCE, S. E. & MAGUIRE, A. R. 2010. 1,3-Dipolar cycloadditions of 2-thio-3-chloroacrylamides with diazoalkanes. Organic & Biomolecular Chemistry, 8, 2735-2748. DOI: 10.1039/C002479A
Published Version: 10.1039/C002479A

Abstract:

2-Thio-3-chloroacrylamides undergo 1,3-dipolar cycloadditions with diazoalkanes leading to a series of novel pyrazolines and pyrazoles. The mechanistic and synthetic features of the cycloadditions to the 2-thio-3-chloroacrylamides at both the sulfide and sulfoxide levels of oxidation are rationalised on the basis of the nature of the substituents.

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