Reaction of 2-(ethoxymethylidene)-3-oxo carboxylic acid esters with tetrazol-5-amine / Goryaeva M. V.,Burgart Ya. V.,Ezhikova M. A.,Kodess M. I.,Saloutin V. I. // RUSSIAN JOURNAL OF ORGANIC CHEMISTRY. - 2015. - V. 51, l. 7. - P. 992-1002.

ISSN/EISSN:

1070-4280 / 1608-3393

Type:

Article

Abstract:

2-(Ethoxymethylidene)-3-oxo carboxylic acid esters reacted with tetrazol-5-amine to give ethyl 4-alkyl-2-azidopyrimidine-5-carboxylates capable of undergoing subsequent nucleophilic substitution of hydrogen on C-6 or azido group. The reaction of ethyl 2-benzoyl-3-ethoxyprop-2-enoate with tetrazol-5-amine was accompanied by partial decomposition to afford a mixture of ethyl 3-oxo-3-phenylpropanoate and ethyl 7-(1-ethoxy-1,3-dioxo-3-phenylpropan-2-yl)-5-phenyl-4,7-dihydrotetrazolo {[}1,5-a]pyrimidine-6-carboxylate. Ethyl 7-hydroxytetrazolo{[}1,5-a]pyrimidine-6-carboxylate was formed as a result of cyclization of diethyl 2-(ethoxymethylidene)propanedioate with tetrazol-5-amine.

Author keywords:

AZIDE-TETRAZOLE EQUILIBRIUM; RING-CHAIN ISOMERISM; J COUPLINGS; SERIES; ETHYL; NUCLEOPHILES; PYRIMIDINES; C-13-N-15; H-1-N-15

DOI:

10.1134/S1070428015070179

Web of Science ID:

ISI:000359555800017

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUL
Publisher	MAIK NAUKA/INTERPERIODICA/SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013-1578 USA
Language	English
EISSN	1608-3393
Keywords-Plus	AZIDE-TETRAZOLE EQUILIBRIUM; RING-CHAIN ISOMERISM; J COUPLINGS; SERIES; ETHYL; NUCLEOPHILES; PYRIMIDINES; C-13-N-15; H-1-N-15
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	pmv@ios.uran.ru
ResearcherID-Numbers	Burgart, Yanina/T-8025-2017
ORCID-Numbers	Burgart, Yanina/0000-0001-6061-2410
Funding-Acknowledgement	Russian Foundation for Basic Research {[}13-03-00617]; Ural Branch, Russian Academy of Sciences {[}15-21-3-9]; Program for State Support of Leading Scientific Schools {[}3656.2014.3]
Funding-Text	This study was performed under financial support by the Russian Foundation for Basic Research (project no. 13-03-00617), by the Program of the Ural Branch, Russian Academy of Sciences (project no. 15-21-3-9), and by the Program for State Support of Leading Scientific Schools (project no. 3656.2014.3).
Number-of-Cited-References	37
Usage-Count-Since-2013	5
Journal-ISO	Russ. J. Organ. Chem.
Doc-Delivery-Number	CP0HG