Issue 12, 2010
From the journal:

Organic & Biomolecular Chemistry

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

Marie Kissane,a   Simon E. Lawrencea  and  Anita R. Maguire*b  

* Corresponding authors

a Department of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork, Cork, Ireland

b Department of Chemistry & School of Pharmacy, Analytical and Biological Chemistry Research Facility, University College Cork, Cork, Ireland
E-mail: a.maguire@ucc.ie
Fax: +353 21 4274097
Tel: +353 21 4901693

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.

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

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Article information

DOI
https://doi.org/10.1039/C002479A
Article type
Paper
Submitted
10 Feb 2010
Accepted
24 Mar 2010
First published
23 Apr 2010

Org. Biomol. Chem., 2010,8, 2735-2748

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

M. Kissane, S. E. Lawrence and A. R. Maguire, Org. Biomol. Chem., 2010, 8, 2735 DOI: 10.1039/C002479A

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