TY - JOUR

T1 - A Versatile Method for the Synthesis of 7-Aminoazolo[1,5-a]pyrimidine-6-carbonitriles

AU - Urakov, G. V.

AU - Savateev, K. V.

AU - Rusinov, V. L.

N1 - The research funding from the Ministry of Science and Higher Education of the Russian Federation (Ural Federal University project within the Priority-2030 Program) is gratefully acknowledged.

PY - 2022/8/1

Y1 - 2022/8/1

N2 - Nitrile-containing azoloazines with a bridged nitrogen atom are of interest as molecules with potential antiviral and antidiabetic activity. To date, a few corresponding 7-aminoazolo[1,5-a]pyrimidine-6-carbonitriles has been described in the literature and there is no universal method for their synthesis, which limits the possibility to optimize structure for preparing derivatives with prescribed biological activity. In the present work, we have studied different conditions for cyclocondensation of aminoazoles and (ethoxymethylidene)malononotrile; we have shown that optimal method for synthesis of 7-aminoazolo[1,5-a]pyrimidine-6-carbonitriles is the heating of initial components in pyridine. This method provides a library of different nitrileazolopyrimidines containing both electron-donating and electron-withdrawing substituents in the azole fragment.

AB - Nitrile-containing azoloazines with a bridged nitrogen atom are of interest as molecules with potential antiviral and antidiabetic activity. To date, a few corresponding 7-aminoazolo[1,5-a]pyrimidine-6-carbonitriles has been described in the literature and there is no universal method for their synthesis, which limits the possibility to optimize structure for preparing derivatives with prescribed biological activity. In the present work, we have studied different conditions for cyclocondensation of aminoazoles and (ethoxymethylidene)malononotrile; we have shown that optimal method for synthesis of 7-aminoazolo[1,5-a]pyrimidine-6-carbonitriles is the heating of initial components in pyridine. This method provides a library of different nitrileazolopyrimidines containing both electron-donating and electron-withdrawing substituents in the azole fragment.

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85144890463

UR - https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=tsmetrics&SrcApp=tsm_test&DestApp=WOS_CPL&DestLinkType=FullRecord&KeyUT=000925560600003

U2 - 10.1134/S0012500822600304

DO - 10.1134/S0012500822600304

M3 - Article

VL - 505

SP - 168

EP - 176

JO - Doklady Chemistry

JF - Doklady Chemistry

SN - 0012-5008

IS - 2

ER -