Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Syntheses and Some Reactions of 4H-Cyclohepta[4,5]pyrrolo[1,2-α]pyrimidin-4-ones
Noritaka Abe
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1987 Volume 60 Issue 3 Pages 1053-1056

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Abstract

The reaction of 2-aminocyclohepta[b]pyrroles with ethyl acetoacetate in phoshoryl chloride–polyphosphoric acid gives 2-methyl-4H-cyclohepta[4,5]pyrrolo[1,2-a]pyrimidin-4-ones. A ring closure of diethyl N-(cyclohepta[b]pyrrol-2-yl)aminomethylenemalonates gives 4-oxo-4H-cyclohepta[4,5]pyrrolo[1,2-a]pyrimidine-3-carboxylates (2) in phosphoryl chloride–polyphosphoric acid or in hot t-butylbenzene, which are deesterified by the treatment with hot hydrobromic acid. Compounds 2 undergo replacement reactions towards some electrophiles at positions C-3, C-11, and C-7 (in that order).

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