One-pot multicomponent diastereoselective synthesis of novel dihydro-1H-furo[2,3-c]pyrazoles

被引:8
|
作者
Tangeti, Venkata Swamy [1 ]
Prasad, G. V. Siva [1 ]
Panda, Jagadeesh [2 ]
Varma, K. Ramesh [3 ]
机构
[1] Raghu Engn Coll, Vishakhapatnam, India
[2] Raghu Coll Pharm, Vishakhapatnam, India
[3] Sri Venkateswara Univ, Tirupati, India
关键词
Dihydrofuro[1,2-b]pyrazole; microwave synthesis; multicomponent; solvent free; 3-COMPONENT SYNTHESIS; ORGANIC-SYNTHESIS; CHEMISTRY; DRUGS;
D O I
10.1080/00397911.2016.1174781
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient method was developed for the diastereoselective synthesis of novel fused dihydro-1H-furo[2,3-c]pyrazole by a one-pot, four-component reaction of beta-keto ester, hydrazine, aromatic aldehyde, and pyridinium ylide in the presence of triethylamine under microwave irradiation in solvent-free conditions in good yields. The merits of this cascade Knoevenagel condensation/Michael addition/cyclization sequence include its high atom economy, good yields, and efficiency of producing three new bonds (two C-C and one C-O) and two stereocenters in a single operation.
引用
收藏
页码:878 / 884
页数:7
相关论文
共 50 条
  • [1] One-pot, multicomponent synthesis of 4H-pyrano[2,3-c]pyrazoles in water at 25°C
    Reddy, M. B. Madhusudana
    Pasha, M. A.
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2012, 51 (03): : 537 - 541
  • [2] REACTIONS WITH NITRILES - A NOVEL SYNTHESIS OF FURO[2,3-C]PYRAZOLES AND PYRANO[2,3-C]PYRAZOLES
    AZIZ, SI
    ABDALLAH, SO
    IBRAHIM, NS
    HETEROCYCLES, 1984, 22 (11) : 2523 - 2527
  • [3] One-Pot Multicomponent Synthesis of Pyrano[2,3-c]pyrazoles Facilitated by Novel Biocatalyst under Ambient Reaction Conditions
    Kadam, Avdhut
    Deshmukh, Sujit
    Kamble, Santosh
    CHEMISTRYSELECT, 2024, 9 (17):
  • [4] Microwave domino diastereoselective synthesis of novel trans-4,5-dihydro-1H-furo[2,3-c]pyrazoles using pyridinium salts in an aqueous medium
    Yazdani-Elah-Abadi, Afshin
    Morekian, Reza
    Simin, Nasim
    Lashkari, Mojtaba
    JOURNAL OF CHEMICAL RESEARCH, 2018, (04) : 219 - 223
  • [5] One-Pot Synthesis of Novel 2,3-Dihydro-1H-indazoles
    Breton, Gary W.
    Lepore, Antonio J.
    MOLECULES, 2011, 16 (11) : 9553 - 9561
  • [6] Organocatalytic One-Pot Asymmetric Synthesis of 4H,5H-Pyrano[2,3-c]pyrazoles
    Enders, Dieter
    Grossmann, Andre
    Gieraths, Bianca
    Duezdemir, Muharrem
    Merkens, Carina
    ORGANIC LETTERS, 2012, 14 (16) : 4254 - 4257
  • [7] Gluconic acid aqueous solution: A bio-compatible media for one-pot multicomponent synthesis of dihydropyrano [2,3-c] pyrazoles
    Diwan, Furqan
    Shaikh, Mubarak H.
    Fatema, Samreen
    Farooqui, Mazahar
    ORGANIC COMMUNICATIONS, 2019, 12 (04) : 188 - 201
  • [8] One-pot synthesis of 2,3-Dihydro-1H-benzimidazoles
    Ryabukhin, Sergey V.
    Plaskon, Andrey S.
    Volochnyuk, Dmitry M.
    Shivanyuk, Alexander N.
    Tolmachev, Andrey A.
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (19): : 7417 - 7419
  • [9] One-Pot Synthesis of 1,4-Dihydropyrano[2,3-c]pyrazoles Catalyzed by Basic Ionic Liquids
    Li, Xiaojun
    Guo, Hongyun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (01) : 127 - 132
  • [10] Morpholine triflate promoted one-pot, four-component synthesis of dihydropyrano[2,3-c]pyrazoles
    Zhou, Chen-Feng
    Li, Jian-Jun
    Su, Wei-Ke
    CHINESE CHEMICAL LETTERS, 2016, 27 (11) : 1686 - 1690