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Issue 12, 2010
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1,3-Dipolar cycloadditions of 2-thio-3-chloroacrylamides with diazoalkanes

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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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Publication details

The article was received on 10 Feb 2010, accepted on 24 Mar 2010 and first published on 23 Apr 2010


Article type: Paper
DOI: 10.1039/C002479A
Citation: 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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