Synthesis of Dihydrospiro Furo[2,3-c] pyrazoles Promoted by Hypervalent Iodine in Water

被引:8
|
作者
Kale, Ashok [1 ,2 ]
Medishetti, Nagaraju [1 ]
Bingi, Chiranjeevi [1 ]
Atmakur, Krishnaiah [1 ,2 ]
机构
[1] Indian Inst Chem Technol, CSIR, Div Crop Protect Chem, Hyderabad 500007, Andhra Prades, India
[2] Indian Inst Chem Technol, AcSIR, Hyderabad 500007, Andhra Prades, India
关键词
benzaldehydes; pyrazolones; bis(acetoxy) iodobenzene; UNSATURATED PYRAZOLONES; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; MICHAEL ADDITION; CASCADE REACTION; DERIVATIVES; SPIROPYRAZOLONES; ANNULATION; ALKYNES; FUNCTIONALIZATION;
D O I
10.1055/s-0037-1609321
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple, green protocol has been accomplished for the synthesis of dihydrospirofuro[2,3-c] pyrazoles in aqueous medium involving pyrazolone and aldehydes in a one-pot reaction promoted by bis(acetoxy) iodobenzene (BAIB) at ambient temperature. The protocol presented herein describes a new transformation where two molecules of pyrazolone react with an aldehyde in a Knoevenagel condensation followed by a Michael addition, and the resulting dienol was rearranged to the title compound. High compatibility, easy work-up, and excellent yields are the advantages of this protocol.
引用
收藏
页码:1037 / 1042
页数:6
相关论文
共 50 条
  • [1] Divergent synthesis of spirocyclopentene-pyrazolones and pyrano[2,3-c]-pyrazoles via Lewis base controlled annulation reactions
    Luo, Wenjun
    Shao, Bingxuan
    Li, Jingyi
    Song, Dingguo
    Yi, Xiao
    Ling, Fei
    Zhong, Weihui
    TETRAHEDRON LETTERS, 2019, 60 (44)
  • [2] SYNTHESIS OF FURO[2,3-c] PYRIDINE
    Chang, Meng-Yang
    Tai, Hang-Yi
    HETEROCYCLES, 2011, 83 (08) : 1889 - 1896
  • [3] Synthesis of pyrano[2,3-c]pyrazoles: A review
    Sikandar, Sana
    Zahoor, Ameer Fawad
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2021, 58 (03) : 685 - 705
  • [4] Ultrasound promoted green synthesis of spiro[pyrano[2,3-c]pyrazoles] as antioxidant agents
    Dandia, Anshu
    Saini, Deepti
    Bhaskaran, Sumit
    Saini, Dinesh Kumar
    MEDICINAL CHEMISTRY RESEARCH, 2014, 23 (02) : 725 - 734
  • [5] Iodine-mediated efficient synthesis of pyrano[2,3-c]pyrazoles and their antimicrobial activity
    Parshad, Mahavir
    Verma, Vikas
    Kumar, Devinder
    MONATSHEFTE FUR CHEMIE, 2014, 145 (11): : 1857 - 1865
  • [6] A Simple Efficient Procedure for the Synthesis of Benzopyrano[2,3-c]pyrazoles
    Turki, H.
    Kamoun, M.
    Lahiani, S.
    El Gharbi, R.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (05) : 1356 - 1362
  • [7] Enantioselective aminocatalytic synthesis of tetrahydropyrano[2,3-c]pyrazoles via a domino Michael-hemiacetalization reaction with alkylidene pyrazolones
    Maity, Rajendra
    Pan, Subhas Chandra
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (38) : 8032 - 8036
  • [8] A green and practical method for the synthesis of novel pyrano[2,3-c]pyrazoles and bis-pyrano[2,3-c]pyrazoles using sulfonic acid-functionalized ionic liquid
    Farokhian, Pegah
    Mamaghani, Manouchehr
    Mahmoodi, Nosrat Ollah
    Tabatabaeian, Khalil
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2018, 15 (01) : 11 - 16
  • [9] 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
  • [10] Synthesis of Furo[2,3-c]pyridazines via Tandem Transition-Metal Catalysis
    Ganley, Jacob M.
    Waller, David L.
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (23) : 12740 - 12745