Facile access to -acyloxyamides via epoxide rearrangement/three-component domino reaction catalyzed by indium(III) chloride

被引：12
|
作者：
Lingaswamy, Kadari [1 ]
Krishna, Palakodety Radha [1 ]
Prapurna, Y. Lakshmi [1 ]
机构：
[1] Indian Inst Chem Technol, CSIR, Organ & Biomol Chem Div, Discovery Lab, D-207, Hyderabad 500007, Andhra Pradesh, India
来源：
SYNTHETIC COMMUNICATIONS | 2016年 / 46卷 / 15期
关键词：
Epoxides; highly regioselective; indium(III) chloride; tandem rearrangement; Passerini condensation; TosMIC; PASSERINI REACTION; MULTICOMPONENT REACTIONS; 3-COMPONENT REACTION; ISOCYANIDES; CHEMISTRY; ALDEHYDES; KETONES; ACID; ISONITRILES; DIVERSITY;
D O I：
10.1080/00397911.2016.1201511
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and efficient Passerini reaction of epoxides involving highly regioselective rearrangement of epoxide to aldehyde/three-component Passerini reaction catalyzed by indium(III) chloride is described. In the present protocol, epoxides served as wonderful substrates to furnish a library of -acyloxyamides under mild reaction conditions in shorter reaction times and in good yields. [GRAPHICS]
引用
收藏
页码：1275 / 1282
页数：8
相关论文
共 50 条
  • [21] InBr3-catalyzed three-component reaction: a facile synthesis of propargyl amines
    Yadav, J. S.
    Reddy, B. V. Subba
    Gopal, A. V. Hara
    Patil, K. S.
    TETRAHEDRON LETTERS, 2009, 50 (26) : 3493 - 3496
  • [22] Facile synthesis of highly functionalized stable ketenimines via a three-component reaction
    Alizadch, Abdolali
    Rostamnia, Sadegh
    SYNTHESIS-STUTTGART, 2008, (01): : 57 - 60
  • [23] Iron(III)-catalyzed three-component domino strategy for the synthesis of imidazo[1,2-a]pyridines
    Santra, Sougata
    Mitra, Shubhanjan
    Bagdi, Avik Kumar
    Majee, Adinath
    Hajra, Alakananda
    TETRAHEDRON LETTERS, 2014, 55 (37) : 5151 - 5155
  • [24] Bismuth(III) chloride-catalyzed three-component coupling:: Synthesis of α-amino phosphonates
    Zhan, ZP
    Li, JP
    SYNTHETIC COMMUNICATIONS, 2005, 35 (19) : 2501 - 2508
  • [25] Access to sulfonylated furans or imidazo[1,2-a]pyridines via a metal-free three-component, domino reaction
    Cui, Zhiming
    Zhu, Baofu
    Li, Xuechen
    Cao, Hua
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (14): : 2219 - 2223
  • [26] Palladium-catalyzed three-component domino reaction for the preparation of benzo[b]thiophene and related compounds
    Huang, Huanan
    Li, Jing
    Zhao, Weining
    Mei, Yanbo
    Duan, Zheng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (14) : 5036 - 5038
  • [27] Synthesis of Indenes and Benzofulvenes via a Palladium-Catalyzed Three-Component Reaction
    Abel-Snape, Xavier
    Wycich, Gina
    Lautens, Mark
    ACS CATALYSIS, 2022, 12 (06) : 3291 - 3301
  • [28] Synthesis of substituted anilines via a gold-catalyzed three-component reaction
    Ueda, Hirofumi
    Yamamoto, Ryota
    Yamaguchi, Minami
    Tokuyama, Hidetoshi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (04) : 765 - 769
  • [29] N-Heterocyclic Carbene-Catalyzed Three-Component Domino Reaction of Alkynyl Aldehydes with Oxindoles
    Du, Ding
    Hu, Zhongyuan
    Jin, Jianlin
    Lu, Yingyan
    Tang, Weifang
    Wang, Bo
    Lu, Tao
    ORGANIC LETTERS, 2012, 14 (05) : 1274 - 1277
  • [30] Palladium-Catalyzed Three-Component Coupling Reaction via Benzylpalladium Intermediate
    Zhang, Sheng
    Feng, Xiujuan
    Bao, Ming
    CHEMICAL RECORD, 2021, 21 (12): : 3559 - 3572
12345