Palladium-catalyzed regioselective oxidative amination of alkenes: an efficient route to the synthesis of pyrrolocoumarin and pyrroloquinolone derivatives

被引：10

作者：

Majumdar, K. C. ^{[1
]}

Samanta, Srikanta ^{[1
]}

Nandi, Raj Kumar ^{[1
]}

Chattopadhyay, Buddhadeb ^{[1
]}

机构：

[1] Univ Kalyani, Dept Chem, Kalyani 741235, W Bengal, India

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 29期

关键词：

Palladium catalyst; Oxidative amination; 1BX (2-iodoxybenzoic acid); Pyrrolocoumarin; Pyrroloquinolone; ASSISTED INTRAMOLECULAR AMINATION; O-IODOXYBENZOIC ACID; NITROGEN-HETEROCYCLES; QUINOLINE ALKALOIDS; OLEFINS; CYCLIZATION; INDOLES; CYCLOADDITION; REAGENT; ALKYNES;

D O I：

10.1016/j.tetlet.2010.05.068

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-catalyzed IBX-induced intramolecular oxidative amination of alkenes has been utilized for the synthesis of pyrrolocoumarin and pyrroloquinolone derivatives in excellent yields in a short reaction time. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：3807 / 3810

页数：4

共 37 条

[1] Manganese(III) acetate mediated radical reactions leading to araliopsine and related quinoline alkaloids [J].

Bar, G ;

Parsons, AF ;

Thomas, CB .

TETRAHEDRON, 2001, 57 (22) :4719-4728

[2]

Beller M., 1998, TRANSITION METALS OR, V1, P184

[3] Synthesis and absolute stereochemistry assignment of enantiopure dihydrofuro- and dihydropyrano-quinoline alkaloids [J].

Boyd, DR ;

Sharma, ND ;

Barr, SA ;

Carroll, JG ;

Mackerracher, D ;

Malone, JF .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (20) :3397-3405

[4] Design of optical switches as metabolic indicators: New fluorogenic probes for monoamine oxidases (MAO A and B) [J].

Chen, G ;

Yee, DJ ;

Gubernator, NG ;

Sames, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4544-4545

[5] MICROBIAL PYRAN-2-ONES AND DIHYDROPYRAN-2-ONES [J].

DICKINSON, JM .

NATURAL PRODUCT REPORTS, 1993, 10 (01) :71-98

[6]

Fix S.R., 2002, Angew. Chem, V114, P172

[7] PALLADIUM-CATALYZED REACTIONS IN THE SYNTHESIS OF 3-SUBSTITUTED AND 4-SUBSTITUTED INDOLES .2. TOTAL SYNTHESIS OF THE N-ACETYL METHYL-ESTER OF (+/-)-CLAVICIPITIC ACIDS [J].

HARRINGTON, PJ ;

HEGEDUS, LS ;

MCDANIEL, KF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (14) :4335-4338

[8] PALLADIUM-ASSISTED INTRA-MOLECULAR AMINATION OF OLEFINS - SYNTHESIS OF NITROGEN-HETEROCYCLES [J].

HEGEDUS, LS ;

ALLEN, GF ;

BOZELL, JJ ;

WATERMAN, EL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (18) :5800-5807

[9] PALLADIUM-CATALYZED CYCLIZATION OF OMEGA-OLEFINIC TOSAMIDES - SYNTHESIS OF NON-AROMATIC NITROGEN-HETEROCYCLES [J].

HEGEDUS, LS ;

MCKEARIN, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (09) :2444-2451

[10] PALLADIUM ASSISTED INTRAMOLECULAR AMINATION OF OLEFINS - NEW SYNTHESIS OF INDOLES [J].

HEGEDUS, LS ;

ALLEN, GF ;

WATERMAN, EL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (09) :2674-2676

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