It has been established that 2-R-4-oxotetrahydropyrido[4,3-d]pyrimidines, under the action of activated alkynes in methanol, form a mixture of 2-R-4-oxohexahydropyrimido[4,5-d]azocines and products of decomposition of the tetrahydropyridine ring, the 2-R-5-methoxymethyl-4-oxo-6-vinylaminoethyl-pyrimidines. Tetrahydropyrido[3,4-d]pyrimidine, isomeric at the junction of the pyrimidine and tetrahydropyridine rings, forms only the corresponding pyrimido[5,4-d]azocine, the product of expansion, under the action of methyl propiolate.
activated alkyne pyrimidoazocine tandem expansion tandem decomposition
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L. G. Voskressensky, T. N. Borisova, I. S. Kostenev, L. N. Kulikova, and A. V. Varlamov, Tetrahedron Lett., 47, 999 (2006).CrossRefGoogle Scholar
A. H. Cook and K. Y. Reed, J. Heterocycl. Chem., 399 (1945).Google Scholar
L. G. Voskressensky, T. N. Borisova, A. V. Listratova, L. N. Kulikova, A. A. Titov, and A. V. Varlamov, Tetrahedron Lett., 47, 4585 (2006).CrossRefGoogle Scholar
A. Yu. Kuznetsov, Yu. A. Kholopov, S. V. Chapyshev, and N. L. Nam, Izv. Timirjazev. Selsko-Khoz. Akad. No. 2, 119 (2006).Google Scholar