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Vol. 82 2-Amino-5-nitrobenzonitrile dimerizes readily a t 180' in alcoholic ammonia to give 2-(2-amino-5-ni trophenyl)-4-amino-6-nitroquinazoline ( V I 1 1. The structure of VI1 was rigorously confirmed by conversion to 2-(3-nitrophenyl)-6-nitro-4(3H)-quinazolone ( I X ) and t o 2-(2-amino-5-nitrophenyl)-6-nitro-4(3H)-quinazolone ( X I I ) , both of which were then synthesized independently. I t was found t h a t aromatic o-aminonitriles undergo intermolecular condensations with aromatic nitriles in basic media t o give 2-aryl-4-aminoquinazolines in good yield, and t h a t this reaction constitutes a general method for the synthesis of fused 4-aminopyrimidine heterocycles. The mechanisms of these condensation and dimerization reactions are discussed.

The previously reported chlorosulfonation of l-acetyl-5-bromoindoline at the 7-position is in error. In actuality, the 6-substituted product is the sole regioisomer produced. This regiochemical assignment is based on NMR data and confirmed by X-ray analysis. We have prepared the first 7-sulfamoylindoline and the corresponding indole from indoline using the indoline nitrogen to direct sulfamoylation intramolecularly to the 7-position. The new 7-substituted derivatives may prove to be important as intermediates to indole-based dyes and as herbicides.

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