Amination of arenes through electron-deficient reaction cascades of aryl epoxyazides

被引：25

作者：

Lang, S

Kennedy, AR

Murphy, JA

Payne, AH

机构：

[1] Univ Strathclyde, Dept Pure & Appl Chem, Glasgow G1 1XL, Lanark, Scotland

[2] GlaxoSmithKline, Harlow CM19 5AW, Essex, England

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 20期

关键词：

D O I：

10.1021/ol035319d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aryl epoxyazides undergo efficient electron-deficient reaction cascades mediated by Lewis acids, leading to regiospecific amination of the aromatic ring.

引用

页码：3655 / 3658

页数：4

共 30 条

[21] SYNTHESIS OF AMINES BY THE INTERMOLECULAR SCHMIDT REACTION OF ALIPHATIC AZIDES WITH CARBOCATIONS [J].

PEARSON, WH ;

FANG, WK .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (16) :4960-4961

[22] INTRAMOLECULAR SCHMIDT REACTIONS OF AZIDES WITH CARBOCATIONS - SYNTHESIS OF BRIDGED-BICYCLIC AND FUSED-BICYCLIC TERTIARY-AMINES [J].

PEARSON, WH ;

WALAVALKAR, R ;

SCHKERYANTZ, JM ;

FANG, WK ;

BLICKENSDORF, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10183-10194

[23] The intramolecular Schmidt reaction of azides with tertiary alcohols: Synthesis of 5(alpha-naphthyl)- and 5-(beta-naphthyl)indolizidines as potential dopamine analogs and non-opiate antinociceptive agents [J].

Pearson, WH ;

Gallagher, BM .

TETRAHEDRON, 1996, 52 (37) :12039-12048

[24] AN INTRAMOLECULAR SCHMIDT REACTION OF AN ALKYL AZIDE WITH A CARBOCATION - THE GENERATION AND REARRANGEMENT OF A CONFORMATIONALLY RESTRICTED SECONDARY AMINODIAZONIUM ION [J].

PEARSON, WH ;

SCHKERYANTZ, JM .

TETRAHEDRON LETTERS, 1992, 33 (37) :5291-5294

[25] A Schmidt route to 1-azabicyclo[x.y.0]alkanes: a comparison of carbocation stabilizing groups [J].

Pearson, WH ;

Walavalkar, R .

TETRAHEDRON, 2001, 57 (24) :5081-5089

[26] Epoxide-initiated electrophilic cyclization of azides:: A novel route for the stereloselective construction of azabicyclic ring systems and total synthesis of (±)-indolizidine 167B and 209D [J].

Reddy, PG ;

Varghese, B ;

Baskaran, S .

ORGANIC LETTERS, 2003, 5 (04) :583-585

[27] Pentalenene synthase. Analysis of active site residues by site-directed mutagenesis [J].

Seemann, M ;

Zhai, GZ ;

de Kraker, JW ;

Paschall, CM ;

Christianson, DW ;

Cane, DE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (26) :7681-7689

[28] Unparalleled rates for the activation of aryl chlorides and bromides: Coupling with amines and boronic acids in minutes at room temperature [J].

Stambuli, JP ;

Kuwano, R ;

Hartwig, JF .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (24) :4746-4748

[29] Toward the synthesis of sparteine: Intramolecular Schmidt reactions on a norbornanone platform [J].

Wendt, JA ;

Aube, J .

TETRAHEDRON LETTERS, 1996, 37 (10) :1531-1534

[30] Intramolecular reactions of benzylic azides with ketones:: Competition between Schmidt and mannich pathways [J].

Wrobleski, A ;

Aubé, J .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) :886-889

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