Preparation of tricyclic nitrogen heterocycles via intramolecular Diels-Alder reaction of furans

被引:36
作者
Paulvannan, K [1 ]
Jacobs, JW [1 ]
机构
[1] Affymax Res Inst, Santa Clara, CA 95051 USA
关键词
acylation; anhydrides; cycloadditions; Diels-Alder reactions; dienes; epoxidation; furans; lactams; substituent effects;
D O I
10.1016/S0040-4020(99)00390-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Preparation of rigid tricyclic nitrogen heterocycles through acylation of N-alkylfurfurylamines with fumaric and maleic acid derivatives has been studied. The reaction proceeds via an initial amide formation followed by an intramolecular Diels-Alder (IMDA) reaction. Various acylation conditions have been studied. Influence of steric and electronic effects on the product formation has also been investigated. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7433 / 7440
页数:8
相关论文
共 36 条
  • [1] Diastereoselective intramolecular Diels-Alder reaction of the furan diene, a facile access to enantiopure epoxy tetrahydroisoindolines.
    Andres, C
    Maestro, G
    Nieto, J
    Pedrosa, R
    GarciaGranda, S
    PerezCarreno, E
    [J]. TETRAHEDRON LETTERS, 1997, 38 (08) : 1463 - 1466
  • [2] Combinatorial modification of natural products: Preparation of unencoded and encoded libraries of Rauwolfia alkaloids
    Atuegbu, A
    Maclean, D
    Nguyen, C
    Gordon, EM
    Jacobs, JW
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 1996, 4 (07) : 1097 - 1106
  • [3] INTRAMOLECULAR DIELS-ALDER REACTION OF VINYLSULFONIC ACID-ESTERS
    BOVENSCHULTE, E
    METZ, P
    HENKEL, G
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (02): : 202 - 203
  • [4] THE INTRAMOLECULAR DIELS-ALDER REACTION
    BRIEGER, G
    BENNETT, JN
    [J]. CHEMICAL REVIEWS, 1980, 80 (01) : 63 - 97
  • [5] Ciganek E., 1984, ORG REACT NY, V32, P1, DOI DOI 10.1002/0471264180.OR032.01
  • [6] STEREOCHEMICAL ASPECTS OF THE INTRAMOLECULAR DIELS-ALDER REACTION
    CRAIG, D
    [J]. CHEMICAL SOCIETY REVIEWS, 1987, 16 (02) : 187 - 238
  • [7] RATE ACCELERATION OF THE INTRAMOLECULAR DIELS-ALDER REACTION WITH FURAN-DIENE BY ANCHORING SUBSTITUTION - THE T-BUTYL EFFECT REVISITED
    DECORTE, F
    NUYTTENS, F
    CAUWBERGHS, S
    DECLERCQ, P
    [J]. TETRAHEDRON LETTERS, 1993, 34 (11) : 1831 - 1832
  • [8] SYNTHETIC APPROACHES TO PHORBOLS VIA THE INTRAMOLECULAR DIELS-ALDER REACTIONS OF FURANS (IMDAF) - OXYGEN BRIDGE CLEAVAGE AND HIGH STEREOCONTROL DURING CYCLOADDITION USING ALPHA'-BENZYLTHIO SUBSTITUTED FURAN SUBSTRATES
    HARWOOD, LM
    ISHIKAWA, T
    PHILLIPS, H
    WATKIN, D
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (07) : 527 - 530
  • [9] INTRAMOLECULAR DIELS-ALDER REACTIONS OF THE FURAN DIENE (IMDAF) - RAPID CONSTRUCTION OF HIGHLY FUNCTIONALIZED ISOQUINOLINE SKELETONS
    HUDLICKY, T
    BUTORA, G
    FEARNLEY, SP
    GUM, AG
    PERSICHINI, PJ
    STABILE, MR
    MEROLA, JS
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (19): : 2393 - 2398
  • [10] JUNG ME, 1988, HETEROCYCLES, V27, P45