Indium(III)-catalyzed tandem reaction with alkynylbenzaldehydes and alkynylanilines to heteroaromatic compounds

被引：78

作者：

Yanada, Reiko ^{[1
]}

Hashimoto, Kana ^{[1
]}

Tokizane, Rie ^{[1
]}

Miwa, Yoshihisa ^{[1
]}

Minami, Hideki

Yanada, Kazuo ^{[2
]}

Ishikura, Minoru ^{[3
]}

Takemoto, Yoshiji ^{[4
]}

机构：

[1] Hiroshima Int Univ, Fac Pharmaceut Sci, Hiroshima 7370112, Japan

[2] Setsunan Univ, Fac Pharmaceut Sci, Osaka 5730101, Japan

[3] Hlth Sci Univ Hokkaido, Fac Pharmaceut Sci, Ishikari, Hokkaido 0610293, Japan

[4] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 13期

关键词：

D O I：

10.1021/jo800474c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Starting from ortho-alkynylbenzaldehydes and ortho-alkynylanilines, In(OTf)(3)-catalyzed synthesis of ring-condensed heteroaromatic compounds was developed via a domino intramolecular nucleophilic attack/intermolecular cycloaddition/dehydration reaction.

引用

页码：5135 / 5138

页数：4

共 44 条

[31] Concise synthesis of 1,2-dihydroisoquinolines and 1H-isochromenes by carbophilic Lewis acid-catalyzed tandem nucleophilic addition and cyclization of 2-(1-alkynyl)arylaldimines and 2-(1-alkynyl)arylaldehydes [J].

Obika, Shingo ;

Kono, Hideki ;

Yasui, Yoshizumi ;

Yanada, Reiko ;

Takemoto, Yoshiji .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (12) :4462-4468

[32] A one-pot access to 6-substituted phenanthridines from fluoroarenes and nitriles via 1,2-arynes [J].

Pawlas, J ;

Begtrup, M .

ORGANIC LETTERS, 2002, 4 (16) :2687-2690

[33] InBr3-catalyzed intramolecular cyclization of 2-alkynylanilines leading to polysubstituted indole and its application to one-pot synthesis of an amino acid precursor [J].

Sakai, N ;

Annaka, K ;

Konakahara, T .

TETRAHEDRON LETTERS, 2006, 47 (05) :631-634

[34] Cascade approach to substituted 6-aryl-phenanthridines from aromatic aldehydes, anilines, and benzenediazonium-2-carboxylate [J].

Shou, Wang-Ge ;

Yang, Yun-Yun ;

Wang, Yan-Guang .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (24) :9241-9243

[35] Theoretical analysis of the high versatility in PtCl2-mediated cycloisomerization of enynes on a common mechanistic basis [J].

Soriano, E ;

Marco-Contelles, J .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (23) :9345-9353

[36] Gold(I) or gold(III) as active species in AuCl3-catalyzed cyclization/cycloaddition reactions?: A DFT study [J].

Straub, BF .

CHEMICAL COMMUNICATIONS, 2004, (15) :1726-1728

[37] Synthesis of pyrrolo-isoquinolines related to the lamellarins using silver-catalyzed Cycloisomerization/Dipolar cycloaddition [J].

Su, Shun ;

Porco, John A., Jr. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (25) :7744-+

[38] Asymmetric alkynylation of aldehydes catalyzed by an In(III)/BINOL complex [J].

Takita, R ;

Yakura, K ;

Ohshima, T ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (40) :13760-13761

[39] A new entry in catalytic alkynylation of aldehydes and ketones: Dual activation of soft nucleophiles and hard electrophiles by an Indium(III) catalyst [J].

Takita, R ;

Fukuta, Y ;

Tsuji, R ;

Ohshima, T ;

Shibasaki, M .

ORGANIC LETTERS, 2005, 7 (07) :1363-1366

[40] Easy access to aryl- and heteroaryl-annulated[a]carbazoles by the indium-catalyzed reaction of 2-arylindoles with propargyl ethers [J].

Tsuchimoto, T ;

Matsubayashi, H ;

Kaneko, M ;

Shirakawa, E ;

Kawakami, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (09) :1336-1340

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