Regioisomeric synthesis of dihydrofuro[2,3-d]pyrimidines in a diastereoselective manner involving nitrogen ylides in one-pot three-component reaction

被引:14
|
作者
Dutta, Leema [1 ]
Sharma, Meenakshi [2 ]
Bhuyan, Pulak J. [1 ]
机构
[1] CSIR North East Inst Sci & Technol, Div Med Chem, Jorhat 785006, Assam, India
[2] AcSIR, New Delhi, India
关键词
Pyrimidine; Furo[2,3-d]pyrimidines; Aldehyde; Pyridinium bromide; Pyridinium ylide; 1,3-DIPOLAR CYCLOADDITION; BIOLOGICAL EVALUATION; ANALOGS; SYNTHASE;
D O I
10.1016/j.tet.2016.08.084
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesized some novel regioisomers of furo[2,3-d]pyrimidines in a diastereoselective manner via one pot three-component reaction of barbituric acids, aryl aldehydes and pyridinium bromides in the presence of triethylamine as base. Both the isomers were obtained in comparable ratio with excellent overall yield. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6654 / 6660
页数:7
相关论文
共 50 条
  • [1] One-pot synthesis of pyrido[2,3-d]pyrimidines via efficient three-component reaction in aqueous media
    Shi, Daqing
    Niu, Liliui
    Shi, Jingwen
    Wang, Xiangshan
    Ji, Shunjun
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (05) : 1083 - 1090
  • [2] A novel three-component one-pot synthesis of pyrano[2,3-d]pyrimidines and pyrido[2,3-d]pyrimidines using microwave heating in the solid state
    Devi, I
    Kumar, BSD
    Bhuyan, PJ
    TETRAHEDRON LETTERS, 2003, 44 (45) : 8307 - 8310
  • [3] Using Kiwi Juice as a Green Biocatalyst for the Synthesis of Pyrano[2,3-d]pyrimidines in the Facile One-pot, Three-Component Reaction
    Tata, Mohsen
    Marandi, Ghasem
    Marjani, Ahmad Poursattar
    BIOINTERFACE RESEARCH IN APPLIED CHEMISTRY, 2023, 13 (01):
  • [4] One-pot, three-component Synthesis of pyrrolo[2,3-d]pyrimidine Derivatives
    Javahershenas, Ramin
    Khalafy, Jabbar
    JOURNAL OF THE MEXICAN CHEMICAL SOCIETY, 2018, 62 (01)
  • [5] A novel one-pot three-component reaction for the synthesis of 5-arylamino-pyrrolo[2,3-d]pyrimidines under microwave irradiation
    Naidu, P. Seetham
    Bhuyan, Pulak J.
    RSC ADVANCES, 2014, 4 (20) : 9942 - 9945
  • [6] Regio and diastereoselective synthesis of functionalized 2,3-dihydrofuro[3,2-c]coumarins via a one-pot three-component reaction
    Altieri, Elisa
    Cordaro, Massimiliano
    Grassi, Giovanni
    Risitano, Francesco
    Scala, Angela
    TETRAHEDRON, 2010, 66 (49) : 9493 - 9496
  • [7] ONE-POT AND THREE-COMPONENT SYNTHESIS OF SOME NOVEL FUNCTIONALIZED CHROMONYL PYRIDO[2,3-d]PYRIMIDINES AS ANTICANCER AGENTS
    Ali, Tarik E.
    Assiri, Mohammed A.
    Shati, Ali A.
    Alfaifi, Mohammad Y.
    Elbehairi, Serag Eldin, I
    El-Kott, Attalla F.
    HETEROCYCLES, 2021, 102 (05) : 930 - 940
  • [8] A three-component synthesis of pyrido[2,3-d]pyrimidines
    Mont, N
    Teixidó, J
    Borrell, JI
    Kappe, CO
    TETRAHEDRON LETTERS, 2003, 44 (29) : 5385 - 5387
  • [9] Synthesis of some novel functionalized dihydropyrido[2,3-d]pyrimidines via an one-pot three-component reaction catalysed by InCl3
    Naidu, P. Seetham
    Borah, Pallabi
    Bhuyan, Pulak J.
    TETRAHEDRON LETTERS, 2012, 53 (31) : 4015 - 4017
  • [10] A one-pot synthesis of pyrido[2,3-d]- and quinolino[2,3-d]pyrimidines
    El-Ahl, AAS
    El Bialy, SAA
    Ismail, MA
    HETEROCYCLES, 2001, 55 (07) : 1315 - +