Phase Transfer Catalysis Assisted Nucleophilic Displacements in Pyrrolopyrimidines
R. D. Shah
Department of Chemistry M. G. Science Institute
drrdshah@yahoo.co.in
Ключевые слова: nucleophilic displacements, phase transfer catalysis, tetraethyl benzyl ammonium bromide, 18-crown-6, aliquat, pyrrolopyrimidines
Страницы: 319-325
Аннотация
Strategy to involve eco friendly phase transfer catalysis (PTC) with nucleophilic displacements has always been of great interest to study. Therefore, comparative studies of chlorination, azidolysis and indirect amination for synthesis of novel 7,9-disubstituted 5-methyl-7H-tetrazolo[1,5-c]pyrrolo[3,2-e]pyrimidines 4 and their ring cleavage to 5,7-disubstituted 2-methyl-4-amino-7H-pyrrolo[2,3-d]pyrimidines 5 have been undertaken with and without PTC. Chlorination of 5,7-disubstituted 2-methyl-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-ones 2 obtained from 1,4-disubstituted 2-amino-3-pyanopyrroles 1, followed by azidolysis of 5,7-disubstituted 2-methyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidines 3 forming 4 and their chemoselective tetrazole ring cleavage to 5 have been carried out with and without PTC. PTC assisted one pot synthesis of 5 directly from 3 have also been reported.
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