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Exploitation of a new route to fused pyrroles: Synthesis of TNP-351, homo-MTA and 5-arylpyrrolo[2,3-d]pyrimidines

✍ Scribed by Edward C. Taylor; Bin Liu

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 185 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)00677-2

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✦ Synopsis

We have developed a new methodology for the construction of pyrrolo[2,3-~pyrimidines that involves Michael addition of 2,6-diamino-4(3H)-pyrimidinone or 2,4,6triaminopyrimidines to nitroolefins, followed by a Nef reaction of the resulting adduct to form an intermediate aldehyde that spontaneously cyclizes to the fused pyrrole ring, This methodology has been exploited in a new synthesis of TNP-351, and for the first reported preparation of homo-MTA and of a series of 5-arylpyrrolo [2,3-d]pyrimidines.

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