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

[21]

Povarov L.S., 1967, RUSS CHEM REV+, V36, P656, DOI DOI 10.1070/RC1967V036N09ABEH001680

[22]

Sabitha G, 2001, SYNTHESIS-STUTTGART, P1979

[23]

Shipman M., 1994, CONTEMP ORG SYNTH, P1

[24] SEQUENTIAL TRANSFORMATIONS IN ORGANIC-CHEMISTRY - A SYNTHETIC STRATEGY WITH A FUTURE [J].

TIETZE, LF ;

BEIFUSS, U .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1993, 32 (02) :131-163

[25]

Yadav JS, 2002, SYNLETT, P993

[26] MY-1250, A MAJOR METABOLITE OF THE ANTIALLERGIC DRUG REPIRINAST, INDUCES PHOSPHORYLATION OF A 78-KDA PROTEIN IN RAT MAST-CELLS [J].

YAMADA, N ;

KADOWAKI, S ;

TAKAHASHI, K ;

UMEZU, K .

BIOCHEMICAL PHARMACOLOGY, 1992, 44 (06) :1211-1213

[27] Ytterbium(III) triflate/TMSCI: Efficient catalyst for imino ene reaction [J].

Yamanaka, M ;

Nishida, A ;

Nakagawa, M .

ORGANIC LETTERS, 2000, 2 (02) :159-161

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