[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
收藏
页码：651 / 655
页数：5
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