Open Access
Open access
Beilstein-Institut
Beilstein Journal of Organic Chemistry
,  volume 11 ,  pages 385-391

The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles

Publication type: Journal Article
Publication date: 2015-03-23
Beilstein-Institut
scimago Q2
wos Q3
SJR: 0.482
CiteScore: 3.8
Impact factor: 2.1
ISSN: 18605397
DOI:  10.3762/bjoc.11.44
PubMed ID:  25977712
Organic Chemistry
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.

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Goryaeva M. V. et al. The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles // Beilstein Journal of Organic Chemistry. 2015. Vol. 11. pp. 385-391.
GOST all authors (up to 50) Copy
Goryaeva M. V., Burgart Y. V., Ezhikova M. A., Kodess M. I., Saloutin V. I. The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles // Beilstein Journal of Organic Chemistry. 2015. Vol. 11. pp. 385-391.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.3762/bjoc.11.44
UR - https://doi.org/10.3762/bjoc.11.44
TI - The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles
T2 - Beilstein Journal of Organic Chemistry
AU - Goryaeva, Marina V.
AU - Burgart, Yanina V.
AU - Ezhikova, Marina A
AU - Kodess, Mikhail I.
AU - Saloutin, Viktor I.
PY - 2015
DA - 2015/03/23
PB - Beilstein-Institut
SP - 385-391
VL - 11
PMID - 25977712
SN - 1860-5397
ER -
BibTex
Cite this
BibTex (up to 50 authors) Copy
@article{2015_Goryaeva,
author = {Marina V. Goryaeva and Yanina V. Burgart and Marina A Ezhikova and Mikhail I. Kodess and Viktor I. Saloutin},
title = {The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles},
journal = {Beilstein Journal of Organic Chemistry},
year = {2015},
volume = {11},
publisher = {Beilstein-Institut},
month = {mar},
url = {https://doi.org/10.3762/bjoc.11.44},
pages = {385--391},
doi = {10.3762/bjoc.11.44}
}