The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles / Goryaeva Marina V.,Burgart Yanina V.,Ezhikova Marina A.,Kodess Mikhail I.,Saloutin Viktor I. // BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. - 2015. - V. 11, l. . - P. 385-391.

ISSN/EISSN:

1860-5397 / нет данных

Type:

Article

Abstract:

The interaction of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole is an efficient synthetic approach to novel azaheterocycles. 2-Ethoxymethylidene-3-oxo esters bearing alkyl substituents react with 5-aminotetrazole to form ethyl 2-azido-4-alkylpyrimidine-5-carboxylates which are capable of subsequent nucleophilic substitution. The use of diethyl 2-ethoxymethylidenemalonate in this reaction resulted in ethyl 7-hydroxytetrazolo{[}1,5-a] pyrimidine-6-carboxylate, while ethyl 2-ethoxymethylidenecyanoacetate yielded 5-{[}2,6-diamino-3,5-bis(ethoxycarbonyl) pyridinium-1-yl] tetrazol-1-ide through an alternative pathway. Ethyl 2-benzoyl-3-ethoxyprop-2-enoate reacted with 5-aminotetrazole by two reaction routes to form ethyl 2-benzoyl-3-(1H-tetrazol-5-ylamino) prop-2-enoate and ethyl 7-(1-ethoxy-1,3-dioxo-3-phenylpropan-2-yl)-5-phenyl-4,7-dihydrotetrazolo {[}1,5-a] pyrimidine-6-carboxylate.

Author keywords:

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

DOI:

10.3762/bjoc.11.44

Web of Science ID:

ISI:000351340000001

Соавторы в МНС:

Другие поля

Поле	Значение
Month	MAR 23
Publisher	BEILSTEIN-INSTITUT
Address	TRAKEHNER STRASSE 7-9, FRANKFURT AM MAIN, 60487, GERMANY
Language	English
Keywords-Plus	AZIDE-TETRAZOLE EQUILIBRIUM; RING-CHAIN ISOMERISM; J COUPLINGS; ETHYL; SERIES; 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
Number-of-Cited-References	35
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	10
Journal-ISO	Beilstein J. Org. Chem.
Doc-Delivery-Number	CD8JB