Convenient routes to pyrrolo[3,2-b]-, pyrrolo[3,2-c]-, and pyrrolo[2,3-c]-quinolines, and a study of the pyrolysis of 2-quinolylhydrazones
- 1 January 1976
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 19,p. 2121-2125
- https://doi.org/10.1039/p19760002121
Abstract
A useful one-step synthesis of pyrrolo[3,2-b]quinoline (1) from 3-amino-2-methylquinoline and the preparations of derivatives of pyrrolo[3,2-c]-(12) and pyrrolo[2,3-c]-quinoline (21) are described. Pyrolysis of deoxybenzoin 2-quinolylhydrazone (26) is shown to give 2-aminoquinoline (31), 2,3-diphenylimidazo[1,2-a]quinoline (32), and tetraphenylpyrrole (36); butan-2-one 2-quinolylhydrazone (27) gives the aminoquinoline (31), 2,2′-azoquinoline (35), and what is probably an aminodiquinolylamine (33). The mechanisms of these pyrolyses are discussed.Keywords
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