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

Lookup NU author(s): Dr Ross Harrington


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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. (C) 2012 Elsevier Ltd. All rights reserved.

Publication metadata

Author(s): Harrington RW, Stanforth SP

Publication type: Article

Publication status: Published

Journal: Tetrahedron Letters

Year: 2012

Volume: 53

Issue: 16

Pages: 2111-2113

Print publication date: 18/04/2012

ISSN (print): 0040-4039

ISSN (electronic): 1873-3581

Publisher: Pergamon


DOI: 10.1016/j.tetlet.2012.02.050


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