[3+3] Cyclocondensation of β-carbonyl-substituted 1H-benzo[f]chromenes with 3-amino-1,2,4-triazoles: synthesis of [1,2,4] triazolo [1,5-a] pyrimidines

被引：5

作者：

Osipov, Dmitry, V ^{[1
]}

Korzhenko, Kirill S. ^{[1
]}

Osyanin, Vitaly A. ^{[1
]}

Krasnikov, Pavel E. ^{[1
]}

Klimochkin, Yuri N. ^{[1
]}

机构：

[1] Samara State Tech Univ, 244 Molodogvardeyskaya St, Samara 443100, Russia

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2022年 / 58卷 / 11期

基金：

俄罗斯科学基金会;

关键词：

3-amino-1,2,4-triazoles; beta-carbonyl-substituted 1H-benzo[f]chromenes and 4H-chromenes; 1,2,4]triazolo [1,5-a]pyrimidines; aza-Michael reaction; cascade reactions; 3+3] cyclocondensation; ALPHA-AMINOAZOLES; QUINONE METHIDES; CONDENSATION; REARRANGEMENT; 4H-CHROMENES; HETEROCYCLES; KETONES;

D O I：

10.1007/s10593-022-03129-z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of beta-carbonyl-substituted 1H-benzo[f]chromenes with 3-amino-1,2,4-triazoles provides a new avenue for the preparation of [1,2,4]triazolo[1,5-a]pyrimidines containing a (2-hydroxynaphthalen-1-yl)methyl group at position 6. The reaction of 2-trifluoroacetyl-1H-benzo[f]chromene with 3-amino-5-(methylsulfanyl)-1H-1,2,4-triazole yielded a derivative of a new 4,5,5a,13a-tetrahydro-6H-benzo-[5,6]chromeno[3,2-e][1,2,4]triazolo[1,5-a]pyrimidine heterocyclic system. The proposed cascade reaction mechanism includes an aza-Michael reaction, cyclodehydration, and a retro-oxa-Michael reaction.

引用

页码：651 / 655

页数：5

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