Cyclization of ethyl [cyano(4,6-dimethylpyrimidin-2-yl)amino]-acetate

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Resumo

Imidazolin-4-one derivatives have been prepared by a reaction of ethyl [cyano(4,6-dimethylpyrimidin-2-yl)amino]acetate (2) with morpholine, piperidine and hydrazides. In the presence of sulfuric acid, cyanoester 2 gives 2-iminooxazolin-5-one which is acylated on the nitrogen atom of imino group and is rearranged to imidzolidin-2,4-dione in the presence of KCNO.

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Sobre autores

A. Shiryaev

Samara State Technical University

Autor responsável pela correspondência
Email: shiryaev.ak@samgtu.ru
ORCID ID: 0000-0001-9165-869X
Rússia, ul. Molodogvardeiskaya, 244, Samara, 443100

M. Krasavina

Samara State Technical University

Email: shiryaev.ak@samgtu.ru
ORCID ID: 0009-0003-7753-7500
Rússia, ul. Molodogvardeiskaya, 244, Samara, 443100

V. Shiryaev

Samara State Technical University

Email: shiryaev.ak@samgtu.ru
Rússia, ul. Molodogvardeiskaya, 244, Samara, 443100

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2. Scheme 1. Alkylation of (4,6-dimethylpyrimidin-2-yl)cyanamide (1) with ethyl chloroacetate

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3. Scheme 2. Reaction of cyanoester 2 with amines and hydrazides

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4. Scheme 3. Cyclization of cyanoester 2 to imidate 6 and reactions of imidate 6

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5. Scheme 4. Synthesis of ureas 8a, b from cyanamide 1

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6. Scheme 5. Cyclizations of cyanoesters into imidates (TBS – tert-butyldimethylsilyl, PMB – para-methoxybenzyl)

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7. Content

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