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Synthesis of 7 H ‐tetrazolo[1,5‐ c ]pyrrolo[3,2‐ e ]pyrimidines and their reductive ring cleavage to 4‐aminopyrrolo[2,3‐ d ]pyrimidines
Author(s) -
Dave Chaitanya G.,
Shah Rina D.
Publication year - 1998
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570350609
Subject(s) - chemistry , formic acid , sodium azide , ring (chemistry) , cleavage (geology) , medicinal chemistry , azide , stereochemistry , organic chemistry , geotechnical engineering , fracture (geology) , engineering
Abstract Some new 7,9‐disubstituted 7 H ‐1,2,3,4‐tetrazolo[1,5‐ c ]pyrrolo[3,2‐ e ]pyrimidines 5 have been synthesized either by diazotization of 4‐hydrazino‐5,7‐disubstituted‐7 H ‐pyrrolo[2,3‐ d ]pyrimidines 4 obtained by hydrazinolysis of 4‐chloro‐5,7‐disubstituted‐7 H ‐pyrrolo[2,3‐ d ]pyrimidines 3 or via a substitution reaction between 3 and sodium azide. 5,7‐Disubstituted‐7 H ‐pyrrolo[2,3‐ d ]pyrimidin‐4(3 H )‐ones 2 were obtained by cyclocondensation of 2‐amino‐3‐cyano‐1,4‐disubstituted pyrroles 1 with formic acid which on chlorination using phosphorus oxychloride afforded 3 . A novel route for the synthesis of 4‐amino‐5,7‐disubstituted‐7 H ‐pyrrolo[2,3‐ d ]pyrimidines 6 by the reductive ring cleavage of 5 has been reported.