Carbon-nitrogen bond formation in cyclisations by deoxygenation, thermolysis, or photolysis of phenylimidazo[1,2-a]pyridine systems: access to pyrido[1′,2′ : 1,2]imidazo[4,5-b]indoles
- 1 January 1989
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 11,p. 1895-1899
- https://doi.org/10.1039/p19890001895
Abstract
Reductive cyclisation of 2-(2-nitrophenyl)imidazo[1,2-a]pyridine with triethyl phosphite gives the indolic structures (5) and (6). The latter are of interest because of preferential C insertion rather than reaction of the nitrene at N-1 of the imidazole ring. 2D N.m.r. confirms structure (5). Both thermolysis or photolysis of the representative 2-(2-azidophenyl)imidazo[1,2-a]pyridines (7) and (8) are also reported and shown to produce novel indole, cinnoline, and benzofuran structures in an extremely facile fashion.Keywords
This publication has 0 references indexed in Scilit: