Synthesis of novel spiro[benzo[4,5]thiazolo[3,2-a]chromeno[2,3-d] pyrimidine-14,3′-indoline]-1,2′,13(2H)-triones via three component reaction

被引:22
|
作者
Jannati, Saeideh [1 ]
Esmaeili, Abbas Ali [1 ]
机构
[1] Ferdowsi Univ Mashhad, Fac Sci, Dept Chem, Mashhad 9177948974, Iran
关键词
Multicomponent reactions; Cyclohexane-1,3-dione; Tungstophosphoric acid; Spirooxindole; POT 3-COMPONENT SYNTHESIS; N-ALKYL ISATINS; MULTICOMPONENT REACTIONS; THIAZOLOPYRIMIDINE DERIVATIVES; CONVENIENT SYNTHESIS; CONCISE SYNTHESIS; HETEROPOLY ACIDS; EFFICIENT; CHEMISTRY; ANALOGS;
D O I
10.1016/j.tet.2018.04.092
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new and efficient method for the synthesis of hitherto unreported spiro[benzo[4,5]thiazolo[3,2-a] chromeno[2,3-d]pyrimidine-14,3'-indoline]-1,2',13(2H)-triones was developed via the Domino Knoevenagel condensation-Michael addition-intermolecular cyclization sequences of isatin derivatives, cyclohexane-1,3-diones, and 2-hydroxy-4H-benzo14,51thiazolo[3,2-a]pyrimidin-4-ones, employing 12-tungstophosphoric acid (H3PW12O40) as an effective and inexpensive catalyst. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2967 / 2972
页数:6
相关论文
共 50 条
  • [31] p-TSA-promoted syntheses of 5H-benzo[h]thiazolo[2,3-b]quinazoline and indeno[1,2-d]thiazolo[3,2-a]pyrimidine analogs: molecular modeling and in vitro antitumor activity against hepatocellular carcinoma
    Keshari, Amit K.
    Singh, Ashok K.
    Raj, Vinit
    Rai, Amit
    Trivedi, Prakruti
    Ghosh, Balaram
    Kumar, Umesh
    Rawat, Atul
    Kumar, Dinesh
    Saha, Sudipta
    DRUG DESIGN DEVELOPMENT AND THERAPY, 2017, 11 : 1623 - 1642
  • [32] Preparation of benzo[4,5]thiazolo[3,2-a]chromeno[4,3-d]pyrimidin-6-one derivatives using MgO-MgAl2O4 composite nano-powder
    Khalaj, Mehdi
    ARABIAN JOURNAL OF CHEMISTRY, 2020, 13 (08) : 6403 - 6411
  • [33] Synthetic routes for novel annulated chromeno[3,2:5,6]pyrido[2,3-d] imidazo[1,2-a]pyrimidines: Design, characterization, antimicrobial efficiency and theoretical studies
    Abdel-Megid, Mohamed
    Badran, Al-Shimaa
    Ibrahim, Magdy A.
    JOURNAL OF MOLECULAR STRUCTURE, 2025, 1339
  • [34] A regioselective three-component reaction for synthesis of novel 1′H-spiro[isoindoline-1,2′-quinazoline]-3,4′(3′H)-dione derivatives
    Mohammadi, Ali A.
    Dabiri, M.
    Qaraat, H.
    TETRAHEDRON, 2009, 65 (18) : 3804 - 3808
  • [35] Ciprofloxacin-functionalized magnetic silica nanoparticles: as a reusable catalyst for the synthesis of 1H-chromeno[2,3-d]pyrimidine-5-carboxamides and imidazo[1,2-a]pyridines
    Soleimani, Ebrahim
    Torkaman, Sara
    Sepahvand, Heshmatollah
    Ghorbani, Somayeh
    MOLECULAR DIVERSITY, 2019, 23 (03) : 739 - 749
  • [36] Novel Route for the Synthesis of 5-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-1,3-dimethyl-1H-chromeno[2,3-d]pyrimidine-2,4(3H,5H)-diones
    Dige, Nilam C.
    Mahajan, Prasad G.
    Dhokale, Ramdas K.
    Chinchkar, Sarika M.
    Patil, Mayuri, V
    Pore, Dattaprasad M.
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2019, 51 (06) : 553 - 565
  • [37] Facile synthesis of substituted benzo[d]pyrrolo[2′,3′:4,5] pyrrolo[1,2-a]imidazoles by 2-(1H-benzo[d]imidazol-2-yl)acetonitrile and arylglyoxals
    Alizadeh-Bami, Farzaneh
    Mehrabi, Hossein
    Ranjbar-Karimi, Reza
    MONATSHEFTE FUR CHEMIE, 2022, 153 (10): : 913 - 918
  • [38] Novel heteroannulated chromeno[3′,2′:5,6]pyrido[2,3-d][1,2,4]triazolo[4,3-a] pyrimidines and chromeno[3′′,2′′:5′,6′]pyrido[2′,3′:4,5]pyrimido[2,1-c][1,2,4] triazines: Synthesis, characterization and antimicrobial evaluation
    Allehyani, Esam S.
    SYNTHETIC COMMUNICATIONS, 2022, 52 (05) : 764 - 773
  • [39] Catalyst-Free One-Pot Three-Component Synthesis of Diversely Substituted 5-Aryl-2-oxo-/thioxo-2,3dihydro-1H-benzo[6,7] chromeno[2,3-d] pyrimidine-4,6,11(5H)-triones Under Ambient Conditions
    Brahmachari, Goutam
    Nayek, Nayana
    ACS OMEGA, 2017, 2 (08): : 5025 - 5035
  • [40] Catalyst-free rapid synthesis of benzo[4,5]imidazo[1,2-a]-pyrimidine-3-carboxamides via four-component coupling in one pot
    Shaabani, Ahmad
    Seyyedhamzeh, Mozhdeh
    Ganji, Nasim
    Seik Weng Ng
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2014, 11 (02) : 481 - 487