Microwave assisted synthesis of indole-annulated dihydropyrano[3,4-c] chromene derivatives via hetero-Diels-Alder reaction

被引：30
|
作者：
Jha, Mukund [1 ]
Guy, Stephanie [1 ]
Chou, Ting-Yi [1 ]
机构：
[1] Nipissing Univ, Dept Biol & Chem, N Bay, ON P1B 8L7, Canada
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 33期
基金：
加拿大自然科学与工程研究理事会;
关键词：
Indole; Indolin-2-one; Dihydropyran; Chromene; Benzopyran; Hetero-Diels-Alder; Knoevenagel reaction; COMBINATORIAL LIBRARIES; PRIVILEGED STRUCTURES; TERMINAL ACETYLENES; EFFICIENT SYNTHESIS; NATURAL-PRODUCTS; AQUEOUS-MEDIA;
D O I：
10.1016/j.tetlet.2011.06.052
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient two-step synthesis of indole-annulated dihydropyrano[3,4-c]chromene derivatives is achieved via Knoevenagel condensation of O-propargylated salicylaldehyde derivatives with indolin-2-ones followed by a microwave-assisted intramolecular-hetero-Diels-Alder reaction of the resulting (Z)-3-(2-(prop-2-ynyloxy)benzylidene)indolin-2-ones in the presence of 20 mol % Cul in acetonitrile. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4337 / 4341
页数：5
相关论文
共 50 条
  • [1] Synthesis of Pyrano[3,4-c]chromene Skeleton via CuI-Mediated Domino Knoevenagel Hetero-Diels-Alder Reaction
    Mollazadeh, Marjan
    Khoshkholgh, Malihe Javan
    Balalaie, Saeed
    Rominger, Frank
    Bijanzadeh, Hamid Reza
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 47 (05) : 1200 - 1208
  • [2] An efficient ZnO-catalyzed synthesis of novel indole-annulated thiopyrano-chromene derivatives via Domino Knoevenagel-hetero-Diels-Alder reaction
    Kiamehr, Mostafa
    Moghaddam, Firouz Matloubi
    TETRAHEDRON LETTERS, 2009, 50 (48) : 6723 - 6727
  • [3] Synthesis of Novel Polycyclic Indole-Annulated Thiopyranocoumarin Derivatives via Domino Knoevenagel-Hetero-Diels-Alder Reaction in Aqueous Media
    Moghaddam, Firouz Matloubi
    Kiamehr, Mostafa
    Taheri, Salman
    Mirjafary, Zohreh
    HELVETICA CHIMICA ACTA, 2010, 93 (05) : 964 - 973
  • [4] SYNTHESIS OF AZAANTHRAQUINONE DERIVATIVES VIA A HETERO-DIELS-ALDER REACTION
    NEBOIS, P
    BARRET, R
    FILLION, H
    TETRAHEDRON LETTERS, 1990, 31 (18) : 2569 - 2572
  • [5] Synthesis of novel pentacyclic thiopyrano indole-annulated benzo-δ-sultone derivatives via a domino Knoevenagel-hetero-Diels-Alder reaction in water
    Moghaddam, Firouz Matloubi
    Khodabakhshi, Mohammad Reza
    Kiamehr, Mostafa
    Ghahremannejad, Zahra
    TETRAHEDRON LETTERS, 2013, 54 (21) : 2685 - 2689
  • [6] A domino Knoevenagel hetero-Diels-Alder reaction for the synthesis of polycyclic chromene derivatives and evaluation of their cytotoxicity
    Reddy, B. V. Subba
    Divya, Baddula
    Swain, Manisha
    Rao, T. Prabhakar
    Yadav, J. S.
    Vardhan, M. V. P. S. Vishnu
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (05) : 1995 - 1999
  • [7] A SYNTHESIS OF ANNULATED DIHYDROPYRANS VIA HETERO-DIELS-ALDER REACTION - A SIMPLE APPROACH TO ALBOATRIN MODELS
    KRAUSE, M
    HOFFMANN, HMR
    SYNLETT, 1990, (08) : 485 - 486
  • [8] Enantioselective Hetero-Diels-Alder Reaction and the Synthesis of Spiropyrrolidone Derivatives
    Huang, Yekai
    Li, Yanan
    Sun, Jianan
    Li, Jindong
    Zha, Zhenggen
    Wang, Zhiyong
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (15): : 8464 - 8472
  • [9] Domino-Knoevenagel-hetero-Diels-Alder reactions: an efficient one-step synthesis of indole-annulated thiopyranobenzopyran derivatives
    Majumdar, K. C.
    Taher, Abu
    Ray, Krishanu
    TETRAHEDRON LETTERS, 2009, 50 (27) : 3889 - 3891
  • [10] Facile Synthesis of Furowarfarins via Hetero-Diels-Alder Cycloaddition Reaction
    Soman, Shubhangi S.
    Patel, Jagdish M.
    SYNTHETIC COMMUNICATIONS, 2013, 43 (06) : 775 - 783
12345