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One‐pot synthesis of N 2 ‐aminoprotected 6‐substituted and cycloalka[ d ] 4‐trifluoromethyl‐2‐acetylaminopyrimidines
Author(s) -
Bonacorso Helio G.,
Ferla Adriana,
Cechinel Cleber A.,
Zanatta Nilo,
Martins Marcos A. P.
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.5570450228
Subject(s) - chemistry , trifluoromethyl , acetonitrile , aryl , cycloalkane , alkyl , biphenyl , medicinal chemistry , hydrolysis , solvent , one pot synthesis , stereochemistry , organic chemistry , catalysis
The one‐pot synthesis of a novel series of amino‐protected 6‐alkyl‐, 6‐aryl‐, 6‐heteroaryl‐ and 5,6‐fused‐cycloalkane 4‐trifluoromethyl‐2‐acetylaminopyrimidines, where alkyl = Me; aryl = Ph, 4‐CH 3 Ph, 4‐FPh, 4‐ClPh, 4‐BrPh, 4‐OCH 3 Ph, 4‐NO 2 Ph, 4,4′‐biphenyl, 1‐naphthyl; heteroaryl = 2‐thienyl, 2‐furyl and cycloalkyl = c ‐C 6 H 4 , c ‐C 7 H 5 from the reaction of substituted 4‐methoxy‐1,1,1‐trifluoroalk‐3‐en‐2‐ones with 1‐acetylguanidine in acetonitrile or propan‐2‐ol as solvent, is reported. The acetylamino group of 2‐acetylaminopyrimidines was hydrolyzed under three different conditions to afford the corresponding free 2‐aminopyrimidines.