One-pot domino reactions for synthesis of heterocyclic[3.3.3] propellanes and spiro[cyclopenta[b]pyridine-4,2′-indenes]

被引：28
|
作者：
Zhang, Li-Juan [1 ]
Yan, Chao-Guo [1 ]
机构：
[1] Yangzhou Univ, Coll Chem & Chem Engn, Yangzhou 225002, Peoples R China
来源：
TETRAHEDRON | 2013年 / 69卷 / 24期
基金：
中国国家自然科学基金;
关键词：
Domino reaction; Propellane; Spiro compound; Enaminone; Ninhydrin; DIELS-ALDER REACTION; AROMATIC-ALDEHYDES; METHYL PROPIOLATE; 3-COMPONENT SYNTHESIS; 4-COMPONENT REACTIONS; CATALYZED SYNTHESIS; CYCLIC ENAMINONES; FACILE SYNTHESIS; ONE-STEP; ARYLAMINES;
D O I：
10.1016/j.tet.2013.04.048
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient synthetic procedure for the functionalized heterocyclic[3.3.3]propellanes was successfully developed by one-pot domino reaction of ninhydrin, malononitrile with 3-arylamino-2-cyclohexenones and their 5,5-dimethyl derivatives in the presence of triethylamine in ethanol at room temperature. On the other hand the similar one-pot reaction containing 3-arylamino-2-cyclopentenones resulted in the functionalized spiro[cyclopenta[b]pyridine-4,2'-indenes] in moderate yields. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4915 / 4921
页数：7
相关论文
共 50 条
  • [1] One-pot, three-component synthesis of spiro-[1,8]-naphthyridine derivatives as well as heterocyclic [3.3.3]-propellanes
    Asilpour, Fatemeh
    Saberi, Dariush
    Hasaninejad, Alireza
    TETRAHEDRON, 2024, 160
  • [2] Highly Convergent One-Pot Four-Component Regioselective Synthesis of Spiro-pyranopyrazoles and Oxa-aza-[3.3.3]propellanes
    Alizadeh, Abdolali
    Bayat, Fahimeh
    HELVETICA CHIMICA ACTA, 2014, 97 (05) : 694 - 700
  • [3] A novel and efficient domino reaction for the one-pot synthesis of spiro-2-aminopyrimidinones
    Ramezanpour, Sorour
    Hashtroudi, Mehri Seyed
    Bijanzadeh, Hamid Reza
    Balalaie, Saeed
    TETRAHEDRON LETTERS, 2008, 49 (25) : 3980 - 3982
  • [4] Multistep One-Pot Synthesis of Enantioenriched Polysubstituted Cyclopenta[b]indoles
    Xu, Biao
    Guo, Zhi-Lei
    Jin, Wan-Yan
    Wang, Zhi-Ping
    Peng, Yun-Gui
    Guo, Qi-Xiang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (04) : 1059 - 1062
  • [5] Construction of the cyclopenta[1,3]cyclopropa[1,2-b]naphthalene system in a one-pot domino reactions
    Krohn, K
    Freund, C
    Flörke, U
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1998, 1998 (12) : 2713 - 2718
  • [6] One-pot Three-component Synthesis of Spiro[pyrazolo[3,4-b]pyridine-4,3′-indoline] Derivatives Catalyzed by Melamine Trisulfonic Acid
    Yang, Li-Min
    Sun, Peng-Li
    Wu, Li-Qiang
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2012, 59 (12) : 1500 - 1503
  • [7] ONE-POT SYNTHESIS OF PYRROLO[2,3-B]PYRIDINE DERIVATIVES
    LEVACHER, V
    LEROY, C
    DUPAS, G
    BOURGUIGNON, J
    QUEGUINER, G
    SYNTHETIC COMMUNICATIONS, 1994, 24 (19) : 2697 - 2705
  • [8] One-pot synthesis of novel heterocyclic compounds via tandem reactions
    Huq, C. A. M. A.
    Sivakumar, S.
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2014, 91 (02) : 313 - 317
  • [9] A facile one-pot ultrasound assisted for an efficient synthesis of 1H-spiro[furo[3,4-b]pyridine-4,3′-indoline]-3-carbonitriles
    Ghahremanzadeh, Ramin
    Rashid, Zahra
    Zarnani, Amir-Hassan
    Naeimi, Hossein
    ULTRASONICS SONOCHEMISTRY, 2014, 21 (04) : 1451 - 1460
  • [10] One-pot, sequential four-component synthesis of novel heterocyclic [3.3.3] propellane derivatives at room temperature
    Beyrati, Maryam
    Hasaninejad, Alireza
    RSC ADVANCES, 2018, 8 (26): : 14171 - 14176
12345