A convergent formal [4+2] cycloaddition of 1,6-diynes and benzyl azides: construction of spiro-polyheterocycles

被引：9

作者：

Bao, Ming ^{[1
,2
]}

Lu, Wei ^{[1
,2
]}

Su, Han ^{[1
,2
]}

Qiu, Lihua ^{[1
,2
]}

Xu, Xinfang ^{[1
,2
,3
]}

机构：

[1] Soochow Univ, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China

[2] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Peoples R China

[3] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 17期

基金：

中国国家自然科学基金;

关键词：

CATALYZED CARBENE/ALKYNE METATHESIS; DIELS-ALDER REACTIONS; ACID-PROMOTED REARRANGEMENT; ONE-STEP CONSTRUCTION; ARYLMETHYL AZIDES; CASCADE REACTION; ALKYNE CYCLOADDITION; 2-ALKYNYL ARYLAZIDES; SCHMIDT REACTION; KETONES;

D O I：

10.1039/c8ob00735g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convergent formal [4 + 2] cycloaddition reaction for the construction of structurally appealing spiro-tetrahydroquinolines has been developed, in which, a one-pot reaction is established for the in situ generation of two reagents, a cyclic alkyne and an N-aryliminium ion, from the corresponding precursors in the presence of an Au-catalyst and BrOnsted acid, respectively.

引用

页码：3258 / 3265

页数：8

共 47 条

[1] Gold(I)-Catalyzed Cyclization/Carbonylation Cascade Reaction of 1,6-Diynes: An Access to β,γ-Unsaturated Ketones [J].

Bao, Ming ;

Lu, Wei ;

Cai, Yanping ;

Qiu, Lihua ;

Xu, Xinfang .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (24) :13386-13395

[2] A concise synthesis of quinolinium, and biquinolinium salts and biquinolines from benzylic azides and alkenes promoted by copper(II) species [J].

Chen, Wei-Chen ;

Gandeepan, Parthasarathy ;

Tsai, Chia-Hung ;

Luo, Ching-Zong ;

Rajamalli, Pachaiyappan ;

Cheng, Chien-Hong .

RSC ADVANCES, 2016, 6 (68) :63390-63397

[3] Reactions of alkyl azides and ketones as mediated by Lewis acids:: Schmidt and Mannich reactions using azide precursors [J].

Desai, P ;

Schildknegt, K ;

Agrios, KA ;

Mossman, C ;

Milligan, GL ;

Aubé, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (30) :7226-7232

[4] Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity [J].

Dorel, Ruth ;

Echavarren, Antonio M. .

CHEMICAL REVIEWS, 2015, 115 (17) :9028-9072

[5] α-Substituted vinyl azides: an emerging functionalized alkene [J].

Fu, Junkai ;

Zanoni, Giuseppe ;

Anderson, Edward A. ;

Bi, Xihe .

CHEMICAL SOCIETY REVIEWS, 2017, 46 (23) :7208-7228

[6] FeCl3-catalyzed aza-Diels-Alder reactions of methylenecyclopropanes with imines [J].

Gao, Ke ;

Li, Yizhe ;

Sun, Huixia ;

Fan, Renhua ;

Wu, Jie .

SYNTHETIC COMMUNICATIONS, 2007, 37 (22-24) :4425-4437

[7] Relativistic effects in homogeneous gold catalysis [J].

Gorin, David J. ;

Toste, F. Dean .

NATURE, 2007, 446 (7134) :395-403

[8] Gold(I)-catalyzed intramolecular acetylenic Schmidt reaction [J].

Gorin, DJ ;

Davis, NR ;

Toste, FD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (32) :11260-11261

[9] Gold-catalyzed organic reactions [J].

Hashmi, A. Stephen K. .

CHEMICAL REVIEWS, 2007, 107 (07) :3180-3211

[10] Recent Advances in Reactions of Azides [J].

Huang, Dayun ;

Yan, Guobing .

ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (10) :1600-1619

← 1 2 3 4 5 →