Premium
Synthesis of 4‐(trihalomethyl)dipyrimidin‐2‐ylamines from β‐alkoxy‐α,β‐unsaturated trihalomethyl ketones
Author(s) -
Zanatta Nilo,
Lopes Elizandra C. S.,
Fantinel Leonardo,
Bonacorso Helio G.,
Martins Marcos A. P.
Publication year - 2002
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.5570390514
Subject(s) - chemistry , ketone , medicinal chemistry , acetonitrile , yield (engineering) , pyrimidine , ylide , stereochemistry , organic chemistry , materials science , metallurgy
The synthesis of a novel series of twelve 4‐(trihalomethyl)dipyrimidin‐2‐ylamines, from the cyclo‐condensation reaction of 4‐(trichloromethyl)‐2‐guanidinopyrimidine, with β‐alkoxyvinyl trihalomethyl ketones, of general formula: X 3 C‐C(O)‐C(R 2 )=C(R 1 )‐OR, where: X = F, Cl; R = Me, Et, ‐(CH 2 ) 2 ‐, ‐(CH 2 ) 3 ‐; R 1 = H, Me; R 2 = H, Me, ‐(CH 2 ) 2 ‐, ‐(CH 2 ) 3 ‐, is reported. The reactions were carried out in acetonitrile under reflux for 16 hours, leading to the dipyrimidin‐2‐ylamines in 65‐90% yield. Depending on the substituents of the vinyl ketone, tetrahydropyrimidines or aromatic pyrimidine rings were obtained from the cyclization reaction. When X = Cl, elimination of the trichloromethyl group was observed during the cyclization step. The structure of 4‐(trihalomethyl)dipyrimidin‐2‐ylamines was studied in detail by 1 H‐, 13 C‐ and 2D‐nmr spectroscopy.