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

共 43 条

[1] Cope elimination: Elucidation of solvent effects from QM/MM simulations [J].

Acevedo, Orlando ;

Jorgensen, William L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (18) :6141-6146

[2] Chemoselective acid-catalyzed [4+2]-cycloaddition reactions of ortho-quinone methides and styrenes/stilbenes/cinnamates [J].

Akkarasereenon, Kornkamon ;

Tangdenpaisal, Kassrin ;

Ruchirawat, Somsak ;

Ploypradith, Poonsakdi .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (43) :8854-8866

[3] Isolation of naturally occurring novel isoflavonoids: an update [J].

Al-Maharik, Nawaf .

NATURAL PRODUCT REPORTS, 2019, 36 (08) :1156-1195

[4] Multicomponent Condensation Reactions via ortho-Quinone Methides [J].

Allen, Emily E. ;

Zhu, Calvin ;

Panek, James S. ;

Schaus, Scott E. .

ORGANIC LETTERS, 2017, 19 (07) :1878-1881

[5]

[Anonymous], 2015, CrysAlisPro, version 1.171.38.41

[6] Generation of ortho-Quinone Methides by p-TsOH on Silica and Their Hetero-Diels-Alder Reactions with Styrenes [J].

Batsomboon, Paratchata ;

Phakhodee, Wong ;

Ruchirawat, Somsak ;

Ploypradith, Poonsakdi .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10) :4009-4012

[7]

Bilgiç S, 2007, J CHEM RES-S, P76

[8] ORTHOAMIDES .8. REACTION OF ACTIVATED METHYL GROUPS ON SUBSTITUTED TOLUENES AND HETEROCYCLES WITH AMINAL-TERT-BUTYL ESTER TO YIELD ENAMINES [J].

BREDERECK, H ;

SIMCHEN, G ;

WAHL, R .

CHEMISCHE BERICHTE-RECUEIL, 1968, 101 (12) :4048-+

[9] Recent advances on the synthesis of flavans, isoflavans, and neoflavans [J].

Chinnabattigalla, Sreenivasulu ;

Dakoju, Ravi Kishore ;

Gedu, Satyanarayana .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2021, 58 (02) :415-441

[10] SYNTHESIS AND ANTIRHINOVIRUS ACTIVITY OF CYANO AND AMIDINO SUBSTITUTED FLAVANOIDS [J].

CONTI, C ;

DESIDERI, N ;

ORSI, N ;

SESTILI, I ;

STEIN, ML .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1990, 25 (09) :725-730

← 1 2 3 4 5 →