Abstract
Reaction of 5-methyl-, 5-bromo-, and 5-iodoisatins with phosphoryl chloride gave the corresponding 2,8-disubstituted indolo[2,1-b]quinazoline-6,12-diones in moderate yield. 5,7-Dichloroisatin failed to react with POCl3. Treatment of an equimolar mixture of isatin and 5-bromoisatin with POCl3 afforded indolo[2,1-b]-quinazoline-6,12-dione (tryptanthrin), 2,8-dibromoindolo[2,1-b]quinazoline-6,12-dione, and two isomeric monobromo-substituted tryptanthrin derivatives, the 2-bromo isomer prevailing.
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