The Meisenheimer Reaction of 1, 4, 5, 8??Tetraazaphenanthrene and Benzo [f] Quinoxaline N??Oxides

R Nasielski??Hinkens, F Faucon…

Index: Nasielski-Hinkens, R.; Faucon, F.; Owen, J. P. Bulletin des Societes Chimiques Belges, 1984 , vol. 93, # 11 p. 953 - 960

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Abstract

Abstract 1, 4, 5, 8-Tetraazaphenanthrene-N 1-oxide (II) reacts with POCl 3 to give equivalent amounts of 2-chloro-tetraazaphenanthrene (V) and 9-chloro-tetraazaphenanthrene (VI). Benzo [f] quinoxaline-N 1-oxide (IV) gives with the same reagent 2-chloro-benzo [f] quinoxaline (IX, 57%) and 9-chloro-benzo [f] quinoxaline (X, 15%). This last result suggests that the chloride ion has entered position 9− of II rather than position 10−, in agreement ...