Impact of substituents on the isatin ring on the reaction between isatins with ortho-phenylenediamine

R Dowlatabadi, A Khalaj, S Rahimian…

Index: Dowlatabadi, Reza; Khalaj, Ali; Rahimian, Sima; Montazeri, Maedeh; Amini, Mohsen; Shahverdi, Ahmadreza; Mahjub, Elham Synthetic Communications, 2011 , vol. 41, # 11 p. 1650 - 1658

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Citation Number: 10

Abstract

Abstract The reaction of different substituted isatins with ortho-phenylenediamine in acetic acid has been investigated. While electron-donor substituents on isatin shift the reaction toward classical 6H-indolo [2, 3-b] quinoxaline ring closure, electron-withdrawing groups enhance the formation of 3-(2′-amino-5′-substituted)-quinoxaline-2 (1H)-ones. The structures of all synthesized compounds were assigned by using infrared, mass, 1H NMR, ...