Pyridynes and indolynes as building blocks for functionalized heterocycles and natural products

被引：225

作者：

Goetz, Adam E. ^{[1
]}

Shah, Tejas K. ^{[1
]}

Garg, Neil K. ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 01期

关键词：

(-)-N-METHYLWELWITINDOLINONE C ISOTHIOCYANATE; METHYLWELWITINDOLINONE D ISONITRILE; ENANTIOSPECIFIC TOTAL-SYNTHESIS; NICKEL-CATALYZED AMINATION; PAR SUBSTITUTION ARYNIQUE; CONCISE TOTAL-SYNTHESIS; DIELS-ALDER REACTIONS; TRAPPING REACTIONS; ORGANIC-SYNTHESIS; N-OXIDES;

D O I：

10.1039/c4cc06445c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Heterocyclic arynes, or hetarynes, have been studied for over 100 years. However, challenges associated with observing these reactive species, as well as developing synthetically useful methods for their generation and trapping, have limited their use. This review provides a brief historical perspective on the field of hetarynes, in addition to a discussion of pyridyne and indolyne methodologies. Moreover, this review highlights the use of pyridynes, indolynes, and related strained intermediates in natural product synthesis.

引用

页码：34 / 45

页数：12

共 134 条

[1] A Unified Route to the Welwitindolinone Alkaloids: Total Syntheses of (-)-N-Methylwelwitindolinone C Isothiocyanate, (-)-N-Methylwelwitindolinone C Isonitrile, and (-)-3-Hydroxy-N-methylwelwitindolinone C Isothiocyanate [J].

Allan, Kevin M. ;

Kobayashi, Kenichi ;

Rawal, Viresh H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (03) :1392-1395

[2] THE REACTION OF SODIUM AMIDE WITH ORTHO-CHLOROTRIFLUROMETHYLBENZENE AND META-CHLOROTRIFLUOROMETHYLBENZENE [J].

BENKESER, RA ;

SEVERSON, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (11) :3838-3839

[3] THE PREPARATION OF AROMATIC AMINES WITH SODIUM AMIDE IN LIQUID AMMONIA [J].

BENKESER, RA ;

BUTING, WE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (12) :3011-3014

[4] SYNTHESIS OF 2,2'-BIINDOLYLS BY COUPLING REACTIONS [J].

BERGMAN, J ;

EKLUND, N .

TETRAHEDRON, 1980, 36 (10) :1439-1443

[5] Total Synthesis of N-Methylwelwitindolinone D Isonitrile [J].

Bhat, Vikram ;

Allan, Kevin M. ;

Rawal, Viresh H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (15) :5798-5801

[6] Recent advances in transition-metal-free carbon-carbon and carbon-heteroatom bond-forming reactions using arynes [J].

Bhunia, Anup ;

Yetra, Santhivardhana Reddy ;

Biju, Akkattu T. .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (08) :3140-3152

[7] Total Syntheses of Anominine and Tubingensin A [J].

Bian, Ming ;

Wang, Zhen ;

Xiong, Xiaochun ;

Sun, Yu ;

Matera, Carlo ;

Nicolaou, K. C. ;

Li, Ang .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (19) :8078-8081

[8] Steric Effects Compete with Aryne Distortion To Control Regioselectivities of Nucleophilic Additions to 3-Silylarynes [J].

Bronner, Sarah M. ;

Mackey, Joel L. ;

Houk, K. N. ;

Garg, Neil K. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (34) :13966-13969

[9] Understanding and Modulating Indolyne Regioselectivities [J].

Bronner, Sarah M. ;

Goetz, Adam E. ;

Garg, Neil K. .

SYNLETT, 2011, (18) :2599-2604

[10] Overturning Indolyne Regioselectivities and Synthesis of Indolactam V [J].

Bronner, Sarah M. ;

Goetz, Adam E. ;

Garg, Neil K. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (11) :3832-3835

← 1 2 3 4 5 6 7 8 9 10 →