Dysprosium(III) catalyzed formation of hexahydrofuro[3,2-c]quinolines via 2:1 coupling of dihydrofuran with substituted anilines

被引：58

作者：

Batey, RA ^{[1
]}

Powell, DA ^{[1
]}

Acton, A ^{[1
]}

Lough, AJ ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 45期

基金：

加拿大自然科学与工程研究理事会;

关键词：

quinolines; hetero Diels-Alder; lanthanides; imines; oxonium ions; oxepins; multi-component coupling;

D O I：

10.1016/S0040-4039(01)01726-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel dysprosium(III) catalyzed 2:1 coupling reaction between substituted anilines and 2 equiv. of dihydrofuran that yields substituted hexahydrofuro[3.2-c]quinolines is described. The reaction proceeds via a formal Diets-Alder process between an in situ generated 2-azadiene with another equivalent of dihydrofuran and may proceed either through a stepwise or an asynchronous concerted mechanism. (C) 2001 Published by Elsevier Science Ltd.

引用

页码：7935 / 7939

页数：5

共 22 条

[1] [Anonymous], 1991, Comprehensive Organic Synthesis
[2] Catalytic, asymmetric cyanohydrin synthesis mediated by lanthanide(III) chloride pybox complexes
Aspinall, HC
Greeves, N
Smith, PM
[J]. TETRAHEDRON LETTERS, 1999, 40 (09) : 1763 - 1766
[3] Babu G, 2000, SYNTHESIS-STUTTGART, P661
[4] A three-component coupling protocol for the synthesis of substituted hexahydropyrrolo[3,2-c]quinolines
Batey, RA
Simoncic, PD
Lin, D
Smyj, RP
Lough, AJ
[J]. CHEMICAL COMMUNICATIONS, 1999, (07) : 651 - 652
[5] Synthesis of 2-CF3-tetrahydroquinoline and quinoline derivatives from CF3-N-aryl-aldimine
Crousse, B
Bégué, JP
Bonnet-Delpon, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) : 5009 - 5013
[6] ROLE REVERSAL IN THE CYCLOCONDENSATION OF CYCLOPENTADIENE WITH HETERODIENOPHILES DERIVED FROM ARYL AMINES AND ALDEHYDES - SYNTHESIS OF NOVEL TETRAHYDROQUINOLINES
GRIECO, PA
BAHSAS, A
[J]. TETRAHEDRON LETTERS, 1988, 29 (46) : 5855 - 5858
[7] Recent progress in the synthesis of 1,2,3,4-tetrahydroquinolines
Katritzky, AR
Rachwal, S
Rachwal, B
[J]. TETRAHEDRON, 1996, 52 (48) : 15031 - 15070
[8] Solid support synthesis of polysubstituted tetrahydroquinolines via three-component condensation catalyzed by Yb(OTf)3
Kiselyov, AS
Smith, L
Armstrong, RW
[J]. TETRAHEDRON, 1998, 54 (20) : 5089 - 5096
[9] KOBAYASHI S, 1995, SYNLETT, P233
[10] KOBAYASHI S, 1995, SYNTHESIS-STUTTGART, P1195

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