The unexpected conversion of a thiophene ring into a pyrrole ring via a putative nitrene intermediate |
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| Authors: | Ross W Harrington Stephen P Stanforth |
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| Institution: | 1. School of Chemistry, Bedson Building, Newcastle University, Newcastle-upon-Tyne, NE1 7RU, UK;2. School of Life Sciences, University of Northumbria, Newcastle-upon-Tyne, NE1 8ST, UK |
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| Abstract: | Triethylphosphite induced reductive cyclisation of 1-(2-nitrophenyl)-3,5-di(2-thienyl)pyrazole 6 afforded the expected 1,3-di(2-thienyl)pyrazolo1,2-a]benzotriazole 7 (14%) together with an unexpected product which was shown to be a 2-(2-thienyl)pyrazolo1,5-a]pyrrolo2,1-c]quinoxaline 8 derivative (27%). A mechanism for the extrusion of sulfur during the transformation of heterocycle 6 into product 8 is proposed. |
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