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Synthesis of 3‐aminopyrazolo[3,4‐ d ]pyrimidine derivatives using N ‐bis(methylthio)methylene‐ p ‐toluenesulfonamide
Author(s) -
Tominaga Yoshinori,
Hara Mayumi,
Honkawa Harumasa,
Hosomi Akira
Publication year - 1990
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.5570270515
Subject(s) - malononitrile , methylene , chemistry , cyanoacetamide , pyrimidine , medicinal chemistry , stereochemistry , organic chemistry , catalysis
N ‐Bis(methylthio)methylene‐ p ‐toluenesulfonamide ( 1 ) reacted with active methylene compounds such as malononitrile ( 2a ) and, cyanoacetamide ( 2b ) to give the corresponding 3‐methylthio‐3‐ p ‐toluenesulfonylami‐nopropenenitrile derivatives 3a,b which were found to be convenient starting materials for the synthesis of 3,5‐diaminopyrazole derivatives. Reaction of 3a and 3b with hydrazines gave the corresponding 3,5‐diaminopyrazoles 4a‐e , key intermediates for the synthesis of 3‐aminopyrazolo[3,4‐ d ]pyrimidine derivatives 5a‐d .