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Synthesis of 5‐mono‐ and 5,7‐diamino‐pyrido[2,3‐ d ]‐pyrimidinediones with potential biological activity by regioselective amination
Author(s) -
Van Tinh Dang,
Stadlbauer Wolfgang
Publication year - 2008
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.5570450329
Subject(s) - chemistry , amination , regioselectivity , pyrimidine , alkyl , dimethylformamide , hydrolysis , acetic acid , medicinal chemistry , organic chemistry , reductive amination , stereochemistry , catalysis , solvent
5‐Alkyl‐/arylamino‐ and 5,7‐dialkyl/arylamino‐pyrido[2,3‐ d ]pyrimidine‐2,4‐diones ( 4,5, 7‐9 ) were prepared from the corresponding 5,7‐dichloro‐pyrido[2,3‐ d ]pyrimidine‐2,4‐diones 2 with aliphatic and aromatic amines 3 and 6 in a regioselective reaction. The 7‐monoazides 10 , obtained by azidation of 5‐amino‐7‐chloro derivatives 4 , were converted to iminophosphoranes by reaction with triphenyl‐phosphane via Staudinger reaction. Hydrolysis with aqueous acetic acid produced in one step 7‐unsubstituted‐amino‐pyrido[2,3‐ d ]pyrimidine‐2,4‐diones 12 . In a similar amination reaction, 5‐chloropyrido[2,3‐ d ]pyrimidine‐2,4,7‐triones 13 were aminated and formylated to 5‐alkyl/arylamino‐6‐formyl derivatives 14 ‐ 16 in a combined one‐step‐reaction with bulky arylamines or alkylamines in the presence of dimethylformamide.