Triphenylphosphonium perchlorate as an efficient catalyst for mono- and bis-intramolecular imino Diels-Alder reactions: synthesis of tetrahydrochromanoquinolines

被引：71

作者：

Anniyappan, M ^{[1
]}

Muralidharan, D ^{[1
]}

Perumal, PT ^{[1
]}

机构：

[1] Cent Leather Res Inst, Div Organ Chem, Madras 600020, Tamil Nadu, India

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 18期

关键词：

triphenylphosphonium perchlorate; mono- and bis-IMIDA; hetero-polycyclic systems;

D O I：

10.1016/S0040-4039(03)00707-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Triphenylphosphonium perchlorate (TPP) is found to be an efficient catalyst for the mono- and bis-intramolecular imino Diels-Alder (IMIDA) reaction of aldimines derived from aromatic amines and O-allyl derivatives of salicylaldehydes to afford the corresponding tetrahydrochromano[4,3-b]quinolines in excellent yields and short reaction times under mild conditions. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：3653 / 3657

页数：5

共 27 条

[1] Diastereoselective synthesis of cis-fused pyrano and furanobenzopyrans catalyzed by indium trichloride or triphenyl phosphonium perchlorate [J].

Anniyappan, M ;

Muralidharan, D ;

Perumal, PT .

TETRAHEDRON, 2002, 58 (52) :10301-10307

[2]

[Anonymous], 1991, Comprehensive Organic Synthesis

[3] Convenient synthesis of pyrano[3,2-c]quinolines and indeno[2,1-c] quinolines by imino Diels-Alder reactions [J].

Babu, G ;

Perumal, PT .

TETRAHEDRON LETTERS, 1998, 39 (20) :3225-3228

[4] Imino Diels-Alder reactions catalyzed by indium trichloride (InCl3). Facile synthesis of quinoline and phenanthridinone derivatives. [J].

Babu, G ;

Perumal, PT .

TETRAHEDRON LETTERS, 1997, 38 (28) :5025-5026

[5]

Boger D.L., 1987, HETERO DIELS ALDER M

[6] DIELS-ALDER REACTIONS OF AZADIENES [J].

BOGER, DL .

TETRAHEDRON, 1983, 39 (18) :2869-2939

[7] DDQ-MEDIATED FORMATION OF CARBON-CARBON BONDS - OXIDATION OF IMINES [J].

BORTOLOTTI, B ;

LEARDINI, R ;

NANNI, D ;

ZANARDI, G .

TETRAHEDRON, 1993, 49 (44) :10157-10174

[8] ROLE REVERSAL IN THE CYCLOCONDENSATION OF CYCLOPENTADIENE WITH HETERODIENOPHILES DERIVED FROM ARYL AMINES AND ALDEHYDES - SYNTHESIS OF NOVEL TETRAHYDROQUINOLINES [J].

GRIECO, PA ;

BAHSAS, A .

TETRAHEDRON LETTERS, 1988, 29 (46) :5855-5858

[9] ASYMMETRIC AZA-DIELS-ALDER REACTION - ENANTIOSELECTIVE AND DIASTEREOSELECTIVE REACTION OF IMINE MEDIATED BY CHIRAL LEWIS ACID [J].

HATTORI, K ;

YAMAMOTO, H .

TETRAHEDRON, 1993, 49 (09) :1749-1760

[10]

HELMCHEN G, 1986, MODERN SYNTHETIC MET, V4, P216

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