Synthesis of N-(2-pyridyl)cyanoacetamides and 4-amino-2H-pyrido-[1,2-a]pyrimidin-2-ones from ethyl cyanoacetate and 2-aminopyridine

Synthesis of N-(2-pyridyl)cyanoacetamides and 4-amino-2H-pyrido-[1,2-a]pyrimidin-2-ones from ethyl cyanoacetate and 2-aminopyridine Full article

Journal

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science
ISSN: 2376-8444 , E-ISSN: 0568-5230

Output data

Year: 1990, Volume: 39, Number: 9, Pages: 1918-1923 Pages count : 6 DOI: 10.1007/bf00958262

Authors

Dorokhov V.A. ¹ , Baranin S.V. ¹ , Dib A. ¹ , Bogdanov V.S. ¹ , Yakovlev I.P. ¹ , Stashina G.A. ¹ , Zhulin V.M. ¹

Affiliations

1	N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

The reaction of 2-aminopyridine and 2-aminopicolines with ethyl cyanoacetate under high pressures results in the formation of 4-amino-4H-pyrido[1,2-a]pyrimidin-2-ones. Depending on the structure of the initial pyridine base, heating of a mixture of the above reagents under low vacuum gives either the same products or their isomeric N-(2-pyridyl)cyanoacetamidēs. The mutual transformations of the synthesized isomers were studied; it was found that cyanoacetamides are readily cyclized by the action of an alcoholic solution of HCl into pyrido[1,2-a]pyrimidin-2-ones, while the latter, during sublimation or heating in DMSO, undergo opening of the pyrimidine ring.

Dorokhov V.A. , Baranin S.V. , Dib A. , Bogdanov V.S. , Yakovlev I.P. , Stashina G.A. , Zhulin V.M.
Synthesis of N-(2-pyridyl)cyanoacetamides and 4-amino-2H-pyrido-[1,2-a]pyrimidin-2-ones from ethyl cyanoacetate and 2-aminopyridine
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science. 1990. V.39. N9. P.1918-1923. DOI: 10.1007/bf00958262 OpenAlex

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