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

Marie Kissane; Simon E. Lawrence; Anita R. Maguire

doi:10.1039/c002479a

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

University College Cork

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	2735-2748
Number of pages	14
Journal	Organic and Biomolecular Chemistry
Volume	8
Issue number	12
DOIs	https://doi.org/10.1039/c002479a
Publication status	Published - 21 Jun 2010

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

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.",

author = "Marie Kissane and Lawrence, \{Simon E.\} and Maguire, \{Anita R.\}",

year = "2010",

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doi = "10.1039/c002479a",

language = "English",

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journal = "Organic and Biomolecular Chemistry",

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AU - Kissane, Marie

AU - Lawrence, Simon E.

AU - Maguire, Anita R.

PY - 2010/6/21

Y1 - 2010/6/21

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/77953184049

U2 - 10.1039/c002479a

DO - 10.1039/c002479a

M3 - Article

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AN - SCOPUS:77953184049

SN - 1477-0520

VL - 8

SP - 2735

EP - 2748

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 12

ER -

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

Abstract

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