InCl3-mediated eco-friendly three-component domino reaction for synthesis of highly functionalized triazolylspiroxindolinopyrans and triazolylpyrans under solvent-free conditions

被引：14
|
作者：
Kamalraja, Jayabal [1 ]
Murugasan, Potharaj [1 ]
Perumal, Paramasivan Thirumalai [1 ]
机构：
[1] CSIR, Cent Leather Res Inst, Div Organ Chem, Madras 600020, Tamil Nadu, India
来源：
RSC ADVANCES | 2014年 / 4卷 / 37期
关键词：
DIELS-ALDER REACTIONS; CATALYTIC ASYMMETRIC-SYNTHESIS; CELL CYCLE INHIBITORS; ONE-POT SYNTHESIS; EFFICIENT SYNTHESIS; ORGANIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; ASPERGILLUS-FUMIGATUS; CLICK CHEMISTRY; ATOM ECONOMY;
D O I：
10.1039/c4ra01524j
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A one pot domino protocol has been developed for the efficient synthesis of novel triazolylspiroxindolinopyrans and triazolylpyran derivatives. The synthesis was achieved by reacting phenacyltriazole, isatin/aromatic aldehyde and active methylene compounds in the presence of InCl3 under solvent-free conditions at 100 degrees C. This novel strategy affording biologically relevant heterocyclic compounds presumably involves Knoevenagel condensation/Michael addition/6-exo-dig-cyclisation sequences.
引用
收藏
页码：19422 / 19432
页数：11
相关论文
共 50 条
  • [31] One-pot three-component Mannich reaction catalyzed by iodine under solvent-free conditions
    Li Gang
    Long Ruiling
    Yang Jiangli
    KINETICS AND CATALYSIS, 2011, 52 (03) : 397 - 400
  • [32] A Simple, Efficient, One-Pot Three-Component Domino Synthesis of Hantzsch Pyridines under Solvent-Free Condition
    Nasr-Esfahani, Masoud
    Karami, Bahador
    Behzadi, Masoume
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 46 (05) : 931 - 935
  • [33] An efficient, three-component synthesis of isoindolin-1-one-3-phosphonates under mild and solvent-free conditions
    Adib, Mehdi
    Sheikhi, Ehsan
    Yazzaf, Rozita
    Bijanzadeh, Hamid Reza
    Mirzaei, Peiman
    TETRAHEDRON LETTERS, 2016, 57 (08) : 841 - 844
  • [34] α-cyclisation of tertiary amines:: Synthesis of some novel annelated quinolines via a three-component reaction under solvent-free conditions
    Devi, Lpsita
    Baruah, BiswaJita
    Bhuyan, Pulak J.
    SYNLETT, 2006, (16) : 2593 - 2596
  • [35] Efficient and Facile Three-Component Reaction for the Synthesis of 2-Amine-4,6-diarylpyrimidine Under Solvent-Free Conditions
    Zhuang, Qiya
    Han, HongXia
    Wang, Suhui
    Tu, Shuajiang
    Rong, Liangce
    SYNTHETIC COMMUNICATIONS, 2009, 39 (03) : 516 - 522
  • [36] A green and eco-friendly method for the synthesis of xanthene derivatives using cellulose sulfuric acid under solvent-free conditions
    Azimi, Seyyedeh Cobra
    Abbaspour-Gilandeh, Esmayeel
    IRANIAN CHEMICAL COMMUNICATION, 2016, 4 (03) : 245 - 255
  • [37] Highly efficient three-component Strecker-type reaction catalyzed by MgI2 etherate under solvent-free conditions
    Li, Pengcheng
    Zhang, Yongdong
    Chen, Zhili
    Zhang, Xingxian
    TETRAHEDRON LETTERS, 2017, 58 (19) : 1854 - 1858
  • [38] Three-component reaction between benzohydrazide acid, ammonium thiocyanate and acid chlorides under solvent-free conditions
    Hassanabadi, Alireza
    Mosslemin, Mohammad H.
    Anary-Abbasinejad, Mohammad
    Hosseini-Tabatabaei, Mohammad R.
    Mahmoudian, Habibeh
    Tadayonfar, Seyd Ehsan
    JOURNAL OF SULFUR CHEMISTRY, 2011, 32 (04) : 355 - 359
  • [39] Regioselective synthesis of functionalized [1,8]-naphthyridine derivatives via three-component domino reaction under catalyst-free conditions
    Feng, Xian
    Wang, Jian-Jun
    Zhang, Juan-Juan
    Cao, Cheng-Pao
    Huang, Zhi-Bin
    Shi, Da-Qing
    GREEN CHEMISTRY, 2015, 17 (02) : 973 - 981
  • [40] Facile Access to Amido (Thio)xanthates under Eco-Friendly Conditions by One-Pot Three-Component Reaction (3-CR)
    Franz, Max
    Stalling, Timo
    Schaper, Raoul
    Schmidtmann, Marc
    Martens, Juergen
    SYNTHESIS-STUTTGART, 2017, 49 (17): : 4045 - 4054
12345