Synthesis of tryptanthrin (couroupitine) derivatives by reaction of substituted isatins with phosphoryl chloride

Synthesis of tryptanthrin (couroupitine) derivatives by reaction of substituted isatins with phosphoryl chloride

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 POCl 3 . Treatment of an equimolar mixture of isatin and 5-bromoisatin with POCl 3 af...

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Veröffentlicht in:Russian journal of organic chemistry 2012, Vol.48 (1), p.123-126
Hauptverfasser: Moskovkina, T. V., Kalinovskii, A. I., Makhan’kov, V. V.
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Organic Chemistry
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container_title Russian journal of organic chemistry
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creator Moskovkina, T. V.
Kalinovskii, A. I.
Makhan’kov, V. V.
description 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 POCl 3 . Treatment of an equimolar mixture of isatin and 5-bromoisatin with POCl 3 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.
doi_str_mv 10.1134/S1070428012010204
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title Synthesis of tryptanthrin (couroupitine) derivatives by reaction of substituted isatins with phosphoryl chloride
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