N-azirin-3-yl and N-indol-3-yl azaxylylenes |
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| Authors: | C.W.G. Fishwick K.R. Randles R.C. Storr P.W. Manley |
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| Affiliation: | Robert Robinson Laboratories, Liverpool University, P.O.Box 147, Liverpool, L69 3BX UK;Searle Research and Development, P.O.Box 53, Lane End Road, High Wycombe, Bucks, HP12 4HZ. UK |
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| Abstract: | Flash-vacuum pyrolysis of N-(2,3-diphenylazirin-3-yl)dihydrobenzoxainones leads to transient N-azirinyl- and N-indolylazaxylylenes which give 2-arylindoles (5) and dihydroindoloquinolines (8) respectively. 5H-1,4-Benzodiazepines are implicated as the precursors to the indoles via the methylene nitrile ylides (9) and an alternative route to the latter by flash pyrolysis of N-(2-methylphenyl)benzimidoyl chlorides (10) provides a new, simple route to 2-arylindoles. |
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