1,3-Dipolar cycloadditions of 2-thio-3-chloroacrylamides with diazoalkanes.
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.
Kissane
Marie
M
Department of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork, Cork, Ireland.
Lawrence
Simon E
SE
Maguire
Anita R
AR
D000178:Acrylamides / Q000737:chemistry*; D000473:Alkanes / Q000737:chemistry*; D003500:Cyclization; D003979:Diazonium Compounds / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry; D010084:Oxidation-Reduction; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry
D000178:Acrylamides; D000473:Alkanes; D003979:Diazonium Compounds; D006571:Heterocyclic Compounds; D011720:Pyrazoles; D013454:Sulfoxides