The unexpected conversion of a thiophene ring into a pyrrole ring via a putative nitrene intermediate

Harrington, Ross and Stanforth, Stephen (2012) The unexpected conversion of a thiophene ring into a pyrrole ring via a putative nitrene intermediate. Tetrahedron Letters, 53 (16). pp. 2111-2113. ISSN 0040-4039

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Official URL: http://dx.doi.org/10.1016/j.tetlet.2012.02.050

Abstract

Triethylphosphite induced reductive cyclisation of 1-(2-nitrophenyl)-3,5-di(2-thienyl)pyrazole 6 afforded the expected 1,3-di(2-thienyl)pyrazolo[1,2-a]benzotriazole 7 (14%) together with an unexpected product which was shown to be a 2-(2-thienyl)pyrazolo[1,5-a]pyrrolo[2,1-c]quinoxaline 8 derivative (27%). A mechanism for the extrusion of sulfur during the transformation of heterocycle 6 into product 8 is proposed.

Item Type: Article
Uncontrolled Keywords: Heterocyclic mesomeric betaines, reductive cyclisation, nitrenes, Pyrazolo[1,2-a]benzotriazole, Pyrazolo[1,5-a]pyrrolo[2,1-c]quinoxaline, thiophenes, polythiophenes
Subjects: F100 Chemistry
Department: Faculties > Health and Life Sciences > School of Life Sciences > Applied Sciences
Depositing User: Ellen Cole
Date Deposited: 17 Dec 2012 10:31
Last Modified: 10 Aug 2015 11:36
URI: http://nrl.northumbria.ac.uk/id/eprint/10642

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