A short time isomerisation for the synthesis of 3-ylideneoxindoles from Morita-Baylis-Hillman adduct of isatin derivatives with 1-hexyn-3-ol using FeCl3 and K-10 clay

被引：3
|
作者：
Vaithiyanathan, Vadivel [1 ,2 ]
Ravichandran, Ganesan [1 ,2 ]
机构：
[1] Arignar Anna Govt Arts Coll, Dept Chem, Villupuram 605602, Tamil Nadu, India
[2] Thiruvalluvar Univ, Vellore, Tamil Nadu, India
来源：
TETRAHEDRON LETTERS | 2021年 / 75卷
关键词：
Isatin; MBH adduct; Isomerisation; 3-ylideneoxindolel; Alkynol; ISOCYANIDE INSERTION REACTION; STEREOSELECTIVE-SYNTHESIS; ENANTIOSELECTIVE CONSTRUCTION; OXINDOLES; 3-ARYL-3-HYDROXYPYRROLIDIN-2-ONES; CYCLIZATION; CASCADE;
D O I：
10.1016/j.tetlet.2021.153212
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
3-ylideneoxindoles are synthesized from Morita-Baylis-Hillman adduct of isatin derivatives with different alcohols using FeCl3 and K-10 clay under microwave irradiation. The reaction occurs in 3 min. As this work done with the help of FeCl3, K-10 clay and microwave irradiation for short time it is an eco-friendly green synthesis. The details of the work are elaborately discussed in this letter. (C) 2021 Elsevier Ltd. All rights reserved.
引用
收藏
页数：5
相关论文
共 9 条
  • [1] Allylic arylative isomerisation of Morita-Baylis-Hillman adduct of isatin derivatives with arenes using FeCl3 and K-10 clay
    Sivaraman, Sivaprakasam
    Aruljothi, Selvaraj
    Vaithiyanathan, Vadivel
    RESULTS IN CHEMISTRY, 2022, 4
  • [2] Eco-friendly K-10 Clay-Mediated [3+3] Spiroannulation of Morita-Baylis-Hillman Adduct of Isatin with Anthracene: Synthesis of Green Fluorophore Compounds
    Vaithiyanathan, Vadivel
    Sivaraman, Sivaprakasam
    ACS OMEGA, 2023, 9 (01): : 934 - 941
  • [3] A Novel Procedure for the Synthesis of Benzo[b][1,8]naphthyridine-3-carboxylate Derivatives from Morita-Baylis-Hillman Adduct Acetates
    Zhong, Weihui
    Lin, Fuliang
    Chen, Ren'er
    Su, Weike
    SYNTHESIS-STUTTGART, 2009, (14): : 2333 - 2340
  • [4] A Short and Efficient Synthesis of 3-Spiro-α-methylene-γ-butyrolactone Oxindolones from Isomerised Bromo Derivatives of Morita-Baylis-Hillman Adducts
    Shanmugam, Ponnusamy
    Viswambharan, Baby
    SYNLETT, 2008, (18) : 2763 - 2768
  • [5] A novel Mgl2 mediated unusual dimerization-spirocyclopropanation of bromo isomerised Morita-Baylis-Hillman adduct of isatin: a facile synthesis of 3-spirocyclopropane-2-oxindole derivatives
    Lingam, Kandapalam Arun Prasath
    Mandal, Asit Baran
    Shanmugam, Ponnusamy
    TETRAHEDRON LETTERS, 2011, 52 (28) : 3610 - 3613
  • [6] Pyridine Core Activation via 1,5-Electrocyclization of Vinyl Pyridinium Ylides Generated from Bromo Isomerized Morita-Baylis-Hillman Adduct of Isatin and Pyridine: Synthesis of 3-Spirodihydroindolizine Oxindoles
    Viswambharan, Baby
    Selvakumar, Kodirajan
    Madhavan, Suchithra
    Shanmugam, Ponnusamy
    ORGANIC LETTERS, 2010, 12 (09) : 2108 - 2111
  • [7] Unprecedented One-Pot, Domino Tertiary Alcohol Protection-Michael Type Addition of Halides to Morita-Baylis-Hillman Adduct of Isatin with RCOX/K2CO3: Diastereoselective Synthesis of Oxindole Appended β-Halo Esters
    Solaiselvi, Rajarethinam
    Shanmugam, Ponnusamy
    Mandal, Asit Baran
    ORGANIC LETTERS, 2013, 15 (06) : 1186 - 1189
  • [8] Synthesis, characterization, and antifungal activity of novel (Z)-N-(2-cyano-3-phenylprop-2-en-l-y1)-alkyl/aryl-sulfonamides derived from a Morita-Baylis-Hillman adduct
    Tavares, Eder C.
    Rubinger, Mayura M. M.
    Zacchi, Carlos H. C.
    Silva, Simone A.
    Oliveira, Marcelo R. L.
    Guilardi, Silvana
    Alcantara, Antonio F. de C.
    Pilo-Veloso, Dorila
    Zambolim, Laercio
    JOURNAL OF MOLECULAR STRUCTURE, 2014, 1067 : 43 - 51
  • [9] Synthesis of chitosan-graft-poly[2-cyano-1-(pyridin-3-yl)allyl acrylate] copolymer from a novel monomer, prepared using a Morita-Baylis-Hillman reaction, and characterization of its antimicrobial activity
    Khalil, Khaled D.
    Ibrahim, Enas I.
    Al-Sagheer, Fakhreia A.
    POLYMER INTERNATIONAL, 2014, 63 (12) : 2042 - 2051
1