Synthesis of 1,2-dihydropyrrolo[1,2-c]pyrimidin-1-ones

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Mercedes Alvarez, David Fernández and John A. Joule


Abstract

1,2-Dihydropyrrolo[1,2-c]pyrimidin-1-ones 2 have been synthesised from pyrrole. We have developed a versatile procedure for the introduction of substituents into the pyrrolopyrimidinones 2, at positions 5 or 7 as desired, and as required by our plans for the synthesis of the variolin type sea alkaloids.


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