Recyclization reactions of 1-alkylpyrimidinium salts.
The reaction of 4-amino-2-benzyl-1-methyl-5-ethoxycarbonylpyrimidinium iodide (3) with alcoholic methylamine resulted in the formation of the methylimine of 2-amino-4-hydroxy-6-methylamino-5-phenylpyridine-3-carbaldehyde (5). Heating of the same pyrimidinium salt in benzylamine gave a mixture of products of two C-C recyclizations: 2-benzyl-4-benzylamino-5-carbamoylpyrimidine (7) and the benzylimine of 4-amino-2-benzyl-6-benzylaminopyrimidine-5-carbaldehyde (8). The reaction of 2-amino-1,4-dimethyl-5-ethoxycarbonylpyrimidinium iodide (10) with KOH ethanolic solution gave a single product of C-C-recyclization: 2-amino-5-acetyl-4-hydroxypyrimidine (11).
Departments of Chemistry and Biochemistry, 1306 University Boulevard, University of Arizona, Tucson, AZ 85721, USA.
Ruben S
RS
Vardanyan
Russian-Armenian (Slavonic) State University, 123 H. Emin Street, Yerevan 375051, Republic of Armenia.
Gevork G
GG
Danagulyan
Russian-Armenian (Slavonic) State University, 123 H. Emin Street, Yerevan 375051, Republic of Armenia.
Armen D
AD
Mkrtchyan
Departments of Chemistry and Biochemistry, 1306 University Boulevard, University of Arizona, Tucson, AZ 85721, USA.
Victor J
VJ
Hruby
pyrimidinium salt; recyclization