In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

Irina G. Tkachenko; Sergey A. Komykhov; Vladimir I. Musatov1; Svitlana V. Shishkina; Viktoriya V. Dyakonenko; Vladimir N. Shvets; Mikhail V. Diachkov; Valentyn A. Chebanov; Sergey M. Desenko

doi:10.3762/bjoc.15.231

In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

Irina G. Tkachenko, Sergey A. Komykhov, Vladimir I. Musatov1, Svitlana V. Shishkina, Viktoriya V. Dyakonenko, Vladimir N. Shvets, Mikhail V. Diachkov, Valentyn A. Chebanov, Sergey M. Desenko

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

The three-component reaction of 5-aminotetrazole with aliphatic aldehydes (formaldehyde, acetaldehyde) and acetoacetic ester derivatives in water under microwave irradiation leads to the selective formation of 4,7-dihydrotetrazolo[1,5-a]pyrimidine derivatives. Under similar conditions using 4,4,4-trifluoroacetoacetic ester 5-hydroxy-4,5,6,7-tetrahydrotetrazolo[1,5-a]pyrimidines are obtained. The analogous reaction with acetylacetone requires scandium(III) triflate as catalyst. The antioxidant activity of selected compounds was assayed with 1,1-diphenyl-2-picrylhydrazyl.

Original language	English
Pages (from-to)	2390-2397
Number of pages	8
Journal	Beilstein Journal of Organic Chemistry
Volume	15
DOIs	https://doi.org/10.3762/bjoc.15.231
State	Published - 8 Oct 2019

Bibliographical note

Publisher Copyright:
© 2019 Beilstein-Institut Zur Forderung der Chemischen Wissenschaften. All rights reserved.

Funding

The authors thank the National Academy of Sciences of Ukraine for financial support in the frame of the projects "Creation of modern bases for obtaining and analyzing substances and components of materials for pharmaceutical purposes" (0119U100727) and "Investigation of structural features of nitrogen-containing heterocycles with potential biological activity" (0119U100716) and the Ministry of Education and Science of Ukraine for financial support in the frame of project “Molecular docking for express identification of new potential drugs” (0119U002550).

Funders	Funder number
National Academy of Sciences of Ukraine	0119U100716, 0119U100727
Ministry of Education and Science of Ukraine	0119U002550

Keywords

1,3-dicarbonyl compounds
5-aminotetrazole
Antioxidant activity
Multicomponent synthesis
Tetrazolo[1,5-a]pyrimidines

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10.3762/bjoc.15.231

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title = "In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines",

abstract = "The three-component reaction of 5-aminotetrazole with aliphatic aldehydes (formaldehyde, acetaldehyde) and acetoacetic ester derivatives in water under microwave irradiation leads to the selective formation of 4,7-dihydrotetrazolo[1,5-a]pyrimidine derivatives. Under similar conditions using 4,4,4-trifluoroacetoacetic ester 5-hydroxy-4,5,6,7-tetrahydrotetrazolo[1,5-a]pyrimidines are obtained. The analogous reaction with acetylacetone requires scandium(III) triflate as catalyst. The antioxidant activity of selected compounds was assayed with 1,1-diphenyl-2-picrylhydrazyl.",

keywords = "1,3-dicarbonyl compounds, 5-aminotetrazole, Antioxidant activity, Multicomponent synthesis, Tetrazolo[1,5-a]pyrimidines",

author = "Tkachenko, {Irina G.} and Komykhov, {Sergey A.} and Musatov1, {Vladimir I.} and Shishkina, {Svitlana V.} and Dyakonenko, {Viktoriya V.} and Shvets, {Vladimir N.} and Diachkov, {Mikhail V.} and Chebanov, {Valentyn A.} and Desenko, {Sergey M.}",

year = "2019",

month = oct,

day = "8",

doi = "10.3762/bjoc.15.231",

language = "אנגלית",

volume = "15",

pages = "2390--2397",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

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TY - JOUR

T1 - In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

AU - Tkachenko, Irina G.

AU - Komykhov, Sergey A.

AU - Musatov1, Vladimir I.

AU - Shishkina, Svitlana V.

AU - Dyakonenko, Viktoriya V.

AU - Shvets, Vladimir N.

AU - Diachkov, Mikhail V.

AU - Chebanov, Valentyn A.

AU - Desenko, Sergey M.

PY - 2019/10/8

Y1 - 2019/10/8

N2 - The three-component reaction of 5-aminotetrazole with aliphatic aldehydes (formaldehyde, acetaldehyde) and acetoacetic ester derivatives in water under microwave irradiation leads to the selective formation of 4,7-dihydrotetrazolo[1,5-a]pyrimidine derivatives. Under similar conditions using 4,4,4-trifluoroacetoacetic ester 5-hydroxy-4,5,6,7-tetrahydrotetrazolo[1,5-a]pyrimidines are obtained. The analogous reaction with acetylacetone requires scandium(III) triflate as catalyst. The antioxidant activity of selected compounds was assayed with 1,1-diphenyl-2-picrylhydrazyl.

AB - The three-component reaction of 5-aminotetrazole with aliphatic aldehydes (formaldehyde, acetaldehyde) and acetoacetic ester derivatives in water under microwave irradiation leads to the selective formation of 4,7-dihydrotetrazolo[1,5-a]pyrimidine derivatives. Under similar conditions using 4,4,4-trifluoroacetoacetic ester 5-hydroxy-4,5,6,7-tetrahydrotetrazolo[1,5-a]pyrimidines are obtained. The analogous reaction with acetylacetone requires scandium(III) triflate as catalyst. The antioxidant activity of selected compounds was assayed with 1,1-diphenyl-2-picrylhydrazyl.

KW - 1,3-dicarbonyl compounds

KW - 5-aminotetrazole

KW - Antioxidant activity

KW - Multicomponent synthesis

KW - Tetrazolo[1,5-a]pyrimidines

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SN - 1860-5397

VL - 15

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EP - 2397

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

Abstract

Bibliographical note

Funding

Keywords

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