Premium
One‐Pot, Atom and Step Economy (PASE) Assembly of Trifluoromethylated Pyrimidines from CF 3 ‐Ynones
Author(s) -
Romanov Alexey R.,
Rulev Alexander Yu.,
Ushakov Igor A.,
Muzalevskiy Vasiliy M.,
Nenajdenko Valentine G.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700727
Subject(s) - chemistry , nucleophile , atom economy , intramolecular force , nitrogen atom , pyrimidine , sequence (biology) , combinatorial chemistry , medicinal chemistry , stereochemistry , catalysis , organic chemistry , ring (chemistry) , biochemistry
A highly efficient synthetic method for the preparation of of 6‐trifluoromethylated pyrimidines was developed. The reaction of CF 3 ‐substituted ynones and nitrogen 1,3‐bis(nucleophile)s was employed for the one‐pot assembly of the pyrimidine core. The cascade route proceeded through an aza‐Michael addition, intramolecular cyclization, and dehydration reaction sequence to give the target heterocycles in excellent yields (up to 97 %). When acetamidine was used as the bis(nucleophile), the unexpected addition of two equivalents of the CF 3 ‐substituted ynone to the acetamidine was observed.