A [4+2] cycloaddition of push-pull styrenes to 1,2-naphthoquinone 1-methides: a synthesis of 2-aryl-2,3-dihydro-1H-benzo[f]chromenes

被引：1
|
作者：
Korzhenko, Kirill S. [1 ]
Yushkova, Anastasiya S. [1 ]
Rashchepkina, Darya A. [1 ]
Demidov, Oleg P. [2 ]
Osipov, Dmitry V. [1 ]
Osyanin, Vitaly A. [1 ]
机构：
[1] Samara State Tech Univ, 244 Molodogvardeyskaya St, Samara 443100, Russia
[2] North Caucasus Fed Univ, 1 Pushkina St, Stavropol 355009, Russia
来源：
CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2023年 / 59卷 / 11-12期
基金：
俄罗斯科学基金会;
关键词：
2-aryl-2,3-dihydro-1H-benzo[f]chromenes; isoflavans; 2-naphthol Mannich bases; push-pull styrene; o-quinone methides; Cope reaction; Diels-Alder reaction; ORTHO-QUINONE METHIDES; DIELS-ALDER REACTIONS; ISOFLAVANS; ANNULATION; CHROMANS; ROUTE; EQUOL;
D O I：
10.1007/s10593-024-03267-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A regioselective and trans-diastereoselective method for the preparation of 2-aryl-2,3-dihydro-1H-benzo[f]chromenes based on 2-naphthol Mannich bases as precursors of 1,2-naphthoquinone 1-methides and highly polarized beta-(N,N-dimethylamino)styrene was developed. The resulting cycloadducts were transformed into cyclic acetals and hemiacetals as well as introduced into the Cope reaction leading to 2-aryl-1H-benzo[f]chromenes.
引用
收藏
页码：745 / 751
页数：7
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