Synthesis of polyfunctionalized benzophenones via the reaction of 3-formylchromones with tertiary push-pull enamines

被引：9

作者：

Barkov, Alexey Yu. ^{[1
]}

Korotaev, Vladislav Yu. ^{[1
]}

Kutyashev, Igor B. ^{[1
]}

Sosnovskikh, Vyacheslav Ya. ^{[1
]}

机构：

[1] Ural Fed Univ, Inst Nat Sci, Dept Chem, Ekaterinburg 620000, Russia

来源：

TETRAHEDRON | 2016年 / 72卷 / 16期

关键词：

3-Formylchromones; Enaminones; Benzophenones; HETEROCYCLIC-SYSTEMS; COMBINATORIAL SYNTHESIS; ENOL ETHERS; 4-OXO-4H-1-BENZOPYRAN-3-CARBOXALDEHYDE; DERIVATIVES; CHEMISTRY; ROUTE; BENZOPYRANS;

D O I：

10.1016/j.tet.2016.03.005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Uncatalyzed nucleophilic reaction of 3-formylchromones with tertiary push pull enamines in refluxing acetonitrile gave polyfunctionalized benzophenone derivatives as a result of a [3-1-3] annulation in moderate to good yields. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：2026 / 2033

页数：8

共 38 条

[1] Synthesis of polyketide-type phenols by domino 'Michael/retro-Michael/Aldol' reactions of 3-formylchromones with silyl enol ethers derived from ethyl 3,5-dioxohexanoate [J].

Adeel, Muhammad ;

Nawaz, Muhammad ;

Villinger, Alexander ;

Reinke, Helmut ;

Fischer, Christine ;

Langer, Peter .

TETRAHEDRON, 2009, 65 (21) :4099-4105

[2] Domino Michael/retro-Michael/Mukaiyama-aldol reactions of 1,3-bis-silyl enol ethers with 3-acyl- and 3-formylbenzopyrylium triflates - Synthesis of functionalised 2,4'-dihydroxybenzophenones [J].

Appel, Bettina ;

Rotzoll, Sven ;

Kranich, Remo ;

Reinke, Helmut ;

Langer, Peter .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (16) :3638-3644

[3]

Araya-Maturana R, 2004, J CHIL CHEM SOC, V49, P35, DOI 10.4067/S0717-97072004000100007

[4] Reactions of 4-oxo-4H-1-benzopyran-3-carboxaldehydes with pentane-2,4-dione in acidic medium -: a new route to dihydroxybenzophenone derivatives [J].

Bandyopadhyay, C ;

Sur, KR ;

Patra, R .

JOURNAL OF CHEMICAL RESEARCH, 1998, (12) :802-803

[5] THE COMBINATORIAL SYNTHESIS AND CHEMICAL AND BIOLOGICAL EVALUATION OF A 1,4-BENZODIAZEPINE LIBRARY [J].

BUNIN, BA ;

PLUNKETT, MJ ;

ELLMAN, JA .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (11) :4708-4712

[6] Push-pull enamines in the synthesis of fused azaheterocycles [J].

Dar'in, D. V. ;

Lobanov, P. S. .

RUSSIAN CHEMICAL REVIEWS, 2015, 84 (06) :601-633

[7] Chromone: A Valid Scaffold in Medicinal Chemistry [J].

Gaspar, Alexandra ;

Matos, Maria Joao ;

Garrido, Jorge ;

Uriarte, Eugenio ;

Borges, Fernanda .

CHEMICAL REVIEWS, 2014, 114 (09) :4960-4992

[8] Chemistry and application of 4-oxo-4H-1-benzopyran-3-carboxaldehyde [J].

Ghosh, Chandra Kanta ;

Chakraborty, Amarnath .

ARKIVOC, 2015, :288-361

[9] Chemistry and Application of 4-Oxo-4H-1-benzopyran-3-carboxaldehyde [J].

Ghosh, Chandra Kanta ;

Patra, Amarendra .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (06) :1529-1547

[10]

Ghosh CK, 2004, HETEROCYCLES, V63, P2875

← 1 2 3 4 →