DBU-mediated [4+2] annulations of donoracceptor cyclopropanes with 3-aryl-2-cyanoacrylates for the synthesis of fully substituted anilines

被引：14

作者：

Liu, Jiaming ^{[1
]}

Qian, Siran ^{[1
]}

Su, Zhenjie ^{[1
]}

Wang, Cunde ^{[1
]}

机构：

[1] Yangzhou Univ, Sch Chem & Chem Engn, 180 Siwangting St, Yangzhou 225002, Jiangsu, Peoples R China

来源：

RSC ADVANCES | 2017年 / 7卷 / 61期

基金：

中国国家自然科学基金;

关键词：

DONOR-ACCEPTOR CYCLOPROPANES; 1-CYANOCYCLOPROPANE; 1-ESTERS; POLYSUBSTITUTED BENZENES; STRAIGHTFORWARD APPROACH; CARBENE COMPLEXES; BENZOIC-ACID; RING; BENZANNULATION; CONSTRUCTION; STRATEGY;

D O I：

10.1039/c7ra07230a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A facile synthesis of fully substituted anilines by the DBU-mediated [4 + 2] annulation of donor-acceptor 1,1-dicyano-cyclopropanes with 3-aryl-2-cyanoacrylate has been developed. This reaction involves a highly efficient multiple domino sequence consisting of ring opening of donor-acceptor cyclopropanes, regioselective intermolecular Michael addition, intramolecular nucleophilic addition and aromatization as key unit steps. This transformation provides a straightforward synthetic protocol for constructing fully substituted aniline derivatives. The structure of two typical products was confirmed by X-ray crystallography.

引用

页码：38342 / 38349

页数：8

共 55 条

[1]

Astruc D., 2002, MODERN ARENE CHEM

[2] A green one-pot multicomponent synthesis of 4H-pyrans and polysubstituted aniline derivatives of biological, pharmacological, and optical applications using silica nanoparticles as reusable catalyst [J].

Banerjee, Subhash ;

Horn, Alissa ;

Khatri, Hari ;

Sereda, Grigoriy .

TETRAHEDRON LETTERS, 2011, 52 (16) :1878-1881

[3] [4 + 2] cycloaromatization of 4-bis(methylthio)-3-buten-2-one with active methylene ketones: A simple and facile phenol annulation [J].

Barun, O ;

Nandi, S ;

Panda, K ;

Ila, H ;

Junjappa, H .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) :5398-5401

[4] One-pot three component synthesis of 3,5-disubstituted 2,6-dicyanoaniline derivatives using 4-dimethylaminopyridine (DMAP) as a catalyst [J].

Bhattacharjee, Suchandra ;

Khan, Abu T. .

TETRAHEDRON LETTERS, 2016, 57 (27-28) :2994-2997

[5] [5+1] annulation: A synthetic strategy for highly substituted phenols and cyclohexenones [J].

Bi, XH ;

Dong, DW ;

Liu, Q ;

Pan, W ;

Zhao, L ;

Li, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4578-4579

[6] Synthesis of macrocycles via cobalt-mediated [2+2+2] cycloadditions [J].

Boñaga, LVR ;

Zhang, HC ;

Moretto, AF ;

Ye, H ;

Gauthier, DA ;

Li, J ;

Leo, GC ;

Maryanoff, BE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (10) :3473-3485

[7] Structure and molecular dynamics of crystalline and liquid anthracene and naphthalene: Possible transient rotator phase of naphthalene [J].

Bordat, Patrice ;

Brown, Ross .

JOURNAL OF CHEMICAL PHYSICS, 2009, 130 (12)

[8] Heterocycles from cyclopropanes: applications in natural product synthesis [J].

Carson, Cheryl A. ;

Kerr, Michael A. .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3051-3060

[9] Intramolecular donor-acceptor cyclopropane ring-opening cyclizations [J].

Cavitt, Marchello A. ;

Phun, Lien H. ;

France, Stefan .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (03) :804-818

[10] Synthesis and inhibitory activity of benzoic acid and pyridine derivatives on influenza neuraminidase [J].

Chand, P ;

Kotian, PL ;

Morris, PE ;

Bantia, S ;

Walsh, DA ;

Babu, YS .

BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (07) :2665-2678

← 1 2 3 4 5 6 →