ChemInform Abstract: Amidoalkylation of Phenacylpyrimidines.

N-Functionally substituted imines of polychlorinated (brominated) aldehydes and ketones

“…189 Reactions of various types of monohydroxypyrimidines with N-(benzoyl)trichloroacetaldimine 3a and other acylimines 3, generated in situ from the corresponding tetrachloroethylamides have been studied. 190,191 It was found that 2-hydroxypyrimidines and 4-hydroxypyrimidines containing no substituents at the 2-position form the products of amidoalkylation of the NH group Ð 1-(1-acylamino-2,2,2-trichloroethyl)-2-( 148) and -4-hydroxypyrimidines 149, respectively. 190 In the case of 2-alkyl-4-hydroxypyrimidines, the reaction involves the oxygen atom and gives O-(1-acylamino-2,2,2-trichloroethyl)-4-hydroxypyrimidines 150a ± d; in the opinion of the authors cited, 190 this is due to the steric shielding of both nucleophilic centres at the nitrogen atoms.…”

“…191 C-Amidoalkylation of the closest analogues of pyrimidine 152 Ð 4-dimethylamino-, 4-methyl-, 4-benzoylmethyl-6-(benzoyl)methyl-pyrimidines Ð has been accomplished by introducing these compounds into reactions with N-(1,2,2,2-tetrachloroethyl)amide of 4-chlorobenzoic acid in acetonitrile in the presence of triethylamine. 191 The alkylation involves the benzoylmethylene group and affords compounds of the type 153 Ð 4-dimethylamino-, 4-methyl-, 4-benzoylmethyl-6-[3,3,3-trichloro-2-(4-chlorobenzoylamino)-1-benzoylpropyl]pyrimidines. 191 Under similar conditions, amidoalkylation of some 5-Ruracils by tetrachloroethylamides of benzoic acids involves both nitrogen atoms and affords 1,3-bis[2,2,2-trichloro-1-(4-chlorobenzoylamino)ethyl]-5-R-pyrimidine-2,4-diones 155.…”

“…191 The alkylation involves the benzoylmethylene group and affords compounds of the type 153 Ð 4-dimethylamino-, 4-methyl-, 4-benzoylmethyl-6-[3,3,3-trichloro-2-(4-chlorobenzoylamino)-1-benzoylpropyl]pyrimidines. 191 Under similar conditions, amidoalkylation of some 5-Ruracils by tetrachloroethylamides of benzoic acids involves both nitrogen atoms and affords 1,3-bis[2,2,2-trichloro-1-(4-chlorobenzoylamino)ethyl]-5-R-pyrimidine-2,4-diones 155. 192 The reaction of 2-thiouracil with tetrachloroethylamides in the presence of triethylamine follows a more complex pathway, which includes not only amidoalkylation at the nitrogen and sulfur atoms but also dehydrochlorination; this gives 2-[(1-amido-2,2-dichlorovinyl)thio]-4-(1-amido-2,2,2-trichloroethoxy)pyrimidines 156.…”