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
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 29 条
  • [21] Natural product-like combinatorial libraries based on privileged structures. 3. The "libraries from libraries" principle for diversity enhancement of benzopyran libraries
    Nicolaou, KC
    Pfefferkorn, JA
    Barluenga, S
    Mitchell, HJ
    Roecker, AJ
    Cao, GQ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (41) : 9968 - 9976
  • [22] Natural product-like combinatorial libraries based on privileged structures. 2. Construction of a 10 000-membered benzopyran library by directed split-and-pool chemistry using NanoKans and optical encoding
    Nicolaou, KC
    Pfefferkorn, JA
    Mitchell, HJ
    Roecker, AJ
    Barluenga, S
    Cao, GQ
    Affleck, RL
    Lillig, JE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (41) : 9954 - 9967
  • [23] Identification of a series of tricyclic natural products as potent broad-spectrum inhibitors of metallo-β-lactamases
    Payne, DJ
    Hueso-Rodríguez, JA
    Boyd, H
    Concha, NO
    Janson, CA
    Gilpin, M
    Bateson, JH
    Cheever, C
    Niconovich, NL
    Pearson, S
    Rittenhouse, S
    Tew, D
    Díez, E
    Pérez, P
    de la Fuente, J
    Rees, M
    Rivera-Sagredo, A
    [J]. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2002, 46 (06) : 1880 - 1886
  • [24] SYNTHESIS OF C-14-LABELED AND H-2-LABELED 1,3-DIHYDRO-3,3-DIMETHYL-5-(1,4,5,6-TETRAHYDRO-6-OXO-3-PYRIDAZINYL)-2H-INDOL-2-ONE (LY195115), AN ORALLY EFFECTIVE POSITIVE INOTROPE
    ROBERTSON, DW
    KRUSHINSKI, JH
    KAU, D
    [J]. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1986, 23 (04) : 343 - 354
  • [25] Sundberg R.J., 1984, COMPREHENSIVE HETERO, V4, P313, DOI DOI 10.1016/B978-008096519-2.00056-4
  • [26] Sundberg R.J., 1970, CHEM INDOLES
  • [27] Sundberg R.J., 1996, BEST SYNTHETIC METHO, P7
  • [28] Domino reactions in the synthesis of heterocyclic natural products and analogs
    Tietze, LF
    Rackelmann, N
    [J]. PURE AND APPLIED CHEMISTRY, 2004, 76 (11) : 1967 - 1983
  • [29] Tietze LF, 2005, MULTICOMPONENT REACTIONS, P121, DOI 10.1002/3527605118.ch5