Experimental and Theoretical Studies of a One??Flask Synthesis of 3H??1??Benzazepines from 2??Haloanilines and α, β??Unsaturated Ketones

…, F Mahir, N Pokeza, W Wong, B Kaplan…

Index: Ramig, Keith; Greer, Edyta M.; Szalda, David J.; Razi, Rabail; Mahir, Fahima; Pokeza, Nataliya; Wong, Wei; Kaplan, Benjamin; Lam, Joanne; Mannan, Ayesha; Missak, Christopher; Mai, Dat; Subramaniam, Gopal; Berkowitz, William F.; Prasad, Prakash; Karimi, Sasan; Lo, Ngai Hin; Kudzma, Linas V. European Journal of Organic Chemistry, 2010 , # 12 p. 2363 - 2371

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Citation Number: 3

Abstract

Abstract 3H-1-Benzazepines are prepared in one step from the reaction of 2-fluoro-or 2- chloroaniline and several aryl vinyl ketones. Enones 9a–c gave benzazepines 11a–c as expected, showing that alkyl substitution at C4 and C5 in the benzazepines is possible. However, enone 9d underwent decomposition due to conjugate addition of the 2- fluoroaniline, while enone 10 gave unsaturated imine 12 as the only product able to be ...