Hypervalent Iodine(III)-Mediated Benzannulation of Enamines with Alkynes for the Synthesis of Polysubstituted Naphthalene Derivatives

被引：46

作者：

Gao, Peng ^{[1
]}

Liu, Jinjian ^{[1
]}

Wei, Yunyang ^{[1
]}

机构：

[1] Nanjing Univ Sci & Technol, Sch Chem Engn, Nanjing 210094, Jiangsu, Peoples R China

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 11期

关键词：

N BOND FORMATION; CATALYZED 4+2 BENZANNULATION; IODINE REAGENT; C-H; OXIDATIVE CYCLIZATION; ORGANOIODINE COMPOUND; COUPLING REACTION; REACTIVITY; BIS(TRIFLUOROACETATE); CYCLOADDITION;

D O I：

10.1021/ol401206g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of functionalized 1-amino-2-naphthalenecarboxylic acid derivatives were synthesized from enamines and alkynes via a benzannulation strategy mediated by iodosylbenzene and BF3 center dot Et2O. The advantages of this novel benzannulation process include broad substrate scope, good functional group tolerance, and mild reaction conditions without the use of heavy metals.

引用

页码：2872 / 2875

页数：4

共 60 条

[1] Organocatalytic, Oxidative, Intramolecular C-H Bond Amination and Metal-free Cross-Amination of Unactivated Arenes at Ambient Temperature
Antonchick, Andrey P.
Samanta, Rajarshi
Kulikov, Katharina
Lategahn, Jonas
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) : 8605 - 8608
[2] Hypervalent iodine(III)-induced intramolecular cyclization of α-(aryl)alkyl-β-dicarbonyl compounds:: A convenient synthesis of benzannulated and spirobenzannulated compounds
Arisawa, M
Ramesh, NG
Nakajima, M
Tohma, H
Kita, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01) : 59 - 65
[3] Lewis acid-catalyzed benzannulation via unprecedented [4+2] cycloaddition of o-alkynyl(oxo)benzenes and enynals with alkynes
Asao, N
Nogami, T
Lee, S
Yamamoto, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) : 10921 - 10925
[4] AuBr3- and Cu(OTf)2-catalyzed intramolecular [4+2] cycloaddition of tethered alkynyl and alkenyl enynones and enynals:: A new synthetic method for functionalized polycyclic hydrocarbons
Asao, N
Sato, K
Menggenbateer
Yamamoto, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) : 3682 - 3685
[5] Lewis acid-catalyzed [4+2] benzannulation between enynal units and enols or enol ethers: Novel synthetic tools for polysubstituted aromatic compounds including indole and benzofuran derivatives
Asao, Naoki
Aikawa, Haruo
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (14) : 5249 - 5253
[6] Oxidative Prins-Pinacol Tandem Process Mediated by a Hypervalent Iodine Reagent: Scope, Limitations, and Applications
Beaulieu, Marc-Andre
Guerard, Kimiaka C.
Maertens, Gaetan
Sabot, Cyrille
Canesi, Sylvain
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (22) : 9460 - 9471
[7] Intramolecular Oxidative C-N Bond Formation for the Synthesis of Carbazoles: Comparison of Reactivity between the Copper-Catalyzed and Metal-Free Conditions
Cho, Seung Hwan
Yoon, Jungho
Chang, Sukbok
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (15) : 5996 - 6005
[8] Novel alternative for the N-N bond formation through a PIFA-mediated oxidative cyclization and its application to the synthesis of indazol-3-ones
Correa, A
Tellitu, I
Dominguez, E
SanMartin, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (09) : 3501 - 3505
[9] An advantageous synthesis of new indazolone and pyrazolone derivatives
Correa, Arkaitz
Tellitu, Imanol
Dominguez, Esther
SanMartin, Raul
[J]. TETRAHEDRON, 2006, 62 (48) : 11100 - 11105
[10] Syntheses of isochromane analogues of the michellamines and korupensamines
de Koning, CB
Michael, JP
van Otterlo, WAL
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (05): : 799 - 811

← 1 2 3 4 5 6 →