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

页码：745 / 751

页数：7

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