Efficient new synthesis of N-arylbenzo[b]furo[3,2-d]pyrimidin-4-amines and their benzo[b]thieno[3,2-d]pyrimidin-4-amine analogues via a microwave-assisted Dimroth rearrangement
A useful and rapid access to libraries of N-arylbenzo[b]furo[3,2-d] pyrimidin-4-amines (1) and their novel benzo[b]thieno[3,2-d]pyrimidin-4-amine analogues (2) was investigated for the first time. Title compounds were obtained via microwave-accelerated co
Dimroth Rearrangement and Other Investigations on Benzofuropyrimidines
Synthesis of 3-alkyl- and 3-aryl-3,4-dihydro-4-iminobenzofuropyrimidines (IV-IX) by the reaction of 3-(ethoxymethylene)amino-2-benzofurancarbonitrile (II) with alkyl- and aryl-amines, and their Dimroth type rearrangement to 4-alkyl- and 4-aryl-aminobenzofuropyrimidines (X-XIV) are described.The reactions of II with ammonia and hydrazine hydrate giving 4-aminobenzofuropyrimidine (III) and 3-amino-4-imino-3,4-dihydrobenzofuropyrimidine (XV) respectively have been investigated.Conversion of XV into s-triazolopyrimidobenzofuran (XVI) and 3-amino-2-benzofurancarbonitrile (I) into various 2-alkyl-4-alkoxybenzofuropyrimidines (XVII-XX) is also reported.
Sangapure, S. S.,Agasimundin, Y. S.
p. 115 - 117
(2007/10/02)
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