H. J. Hertog, D. Buurman
Sep 2, 2010
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0
Influential Citations
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Journal
Recueil des Travaux Chimiques des Pays-Bas
Abstract
The isomeric aminobromoquinolines in which amino groups and bromine atoms are attached to the pyridine nucleus were reacted with potassium amide in liquid ammonia at −33°. 2-Amino-3-bromo- and 2-amino-4-bromo-quinoline are converted via 3,4-didehydroquinoline into 2,3-diaminoquinoline together with some 2,4-diaminoquinoline. Ring transformations occur during reactions of 4-amino-2-bromo- and 3-amino-2-bromo-quinoline yielding 4-amino-2-methylquinazoline and 3-cyanoindole, respectively. 3-Amino-4-bromoquinoline yields a meta-rearranged substitution product i.e. 2,3-diaminoquinoline, while 4-amino-3-bromoquinoline does not react under the conditions applied. Mechanisms of the reactions described are discussed.