Green Approach to the Design of Functionalized Medicinally Privileged 4-Aryl-1,4-dihydropyrano[2,3-c]-pyrazole-5-carbonitrile Scaffold

被引:14
|
作者
Ilovaisky, Alexey I. [1 ]
Medvedev, Michael G. [1 ]
Merkulova, Valentina M. [1 ]
Elinson, Michail N. [1 ]
Nikishin, Gennady I. [1 ]
机构
[1] ND Zelinskii Inst Organ Chem, Moscow 119991, Russia
基金
俄罗斯基础研究基金会;
关键词
ONE-POT SYNTHESIS; IDENTIFICATION; HETEROCYCLES; DERIVATIVES; INHIBITORS; FACILE; WATER;
D O I
10.1002/jhet.1737
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
On water multicomponent condensation of aromatic aldehydes, malononitrile, and 3-methyl-2-pyrazoline-5-one in the presence of sodium hydroxide as catalyst leads to 6-amino-3-methyl-4-aryl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles in 85-98% yields.
引用
收藏
页码:523 / 526
页数:4
相关论文
共 50 条
  • [31] Interaction of Lysozyme with 6-Amino-4-aryl-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole: A Fluorescence Auenching Study
    Wu, Hui
    Chen, Xiu-mei
    Wan, Yu
    Lian, Shu-qin
    Ye, Ling
    ASIAN JOURNAL OF CHEMISTRY, 2009, 21 (04) : 2782 - 2788
  • [32] Unexpected Result of Thiophosphorylation of 6-Aminopyrano[2,3-c]pyrazole-5-carbonitrile Derivative
    Dotsenko, V. V.
    Dushenko, V. A.
    Aksenov, N. A.
    Aksenova, I. V.
    Netreba, E. E.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2019, 89 (09) : 1752 - 1759
  • [33] Synthesis of 3-methyl-6-amino-5-cyano-4-aryl-1-phenyl-1,4-dihydropyrano [2,3-c]pyrazole catalysed by KF-montmorillonite
    Wu, Nan
    Li, Xinnian
    Wang, Yumei
    Shi, Daqing
    JOURNAL OF CHEMICAL RESEARCH, 2008, (01) : 16 - 17
  • [34] Unexpected Result of Thiophosphorylation of 6-Aminopyrano[2,3-c]pyrazole-5-carbonitrile Derivative
    V. V. Dotsenko
    V. A. Dushenko
    N. A. Aksenov
    I. V. Aksenova
    E. E. Netreba
    Russian Journal of General Chemistry, 2019, 89 : 1752 - 1759
  • [35] Design, synthesis, and biological evaluation of 2,4-dihydropyrano[2,3-c]pyrazole derivatives as autotaxin inhibitors
    Pantsar, Tatu
    Singha, Prosanta
    Nevalainen, Tapio J.
    Koshevoy, Igor
    Leppanen, Jukka
    Poso, Antti
    Niskanen, Juha M. A.
    Pasonen-Seppanen, Sanna
    Savinainen, Juha R.
    Laitinen, Tuomo
    Laitinen, Jarmo T.
    EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2017, 107 : 97 - 111
  • [36] Molecular docking simulation and anticancer assessment on human breast carcinoma cell line using novel bis(1,4-dihydropyrano[2,3-c] pyrazole-5-carbonitrile) and bis(1,4-dihydropyrazolo[4′,3′: 5,6] pyrano [2,3-b] pyridine-6-carbonitrile) derivatives
    Salama, Soad K.
    Mohamed, Magda F.
    Darweesh, Ahmed F.
    Elwahy, Ahmed H. M.
    Abdelhamid, Ismail A.
    BIOORGANIC CHEMISTRY, 2017, 71 : 19 - 29
  • [37] Ionic liquid [Et3NH][HSO4]-catalyzedMulticomponent Synthesis of 6-amino-4-(substituted phenyl)-3-methyl-2,4-dihydropyrano[2,3-c] pyrazole-5-carbonitrile
    Nimbalkar, Urja D.
    Seijas Vazquez, Julio A.
    Pilar Vazquez, Maria
    Nikalje, Anna Pratima G.
    20TH INTERNATIONAL ELECTRONIC CONFERENCE ON SYNTHETIC ORGANIC CHEMISTRY (ECSOC), 2016,
  • [38] An environmentally friendly synthesis of 1,4-dihydropyrano[2,3-c]pyrazole derivatives catalyzed by tungstate sulfuric acid
    Mahnaz Farahi
    Bahador Karami
    Iman Sedighimehr
    Hamideh Mohamadi Tanuraghaj
    ChineseChemicalLetters, 2014, 25 (12) : 1580 - 1582
  • [39] Novel 1,4-dihydropyrano[2,3-c]pyrazole derivatives: Synthesis, characterization, biological evaluation and in silico study
    Vasava, Mahesh S.
    Bhoi, Manoj N.
    Rathwa, Sanjay K.
    Shetty, Shilpa S.
    Patel, Rikin D.
    Rajani, Dhanji P.
    Rajani, Smita D.
    Patel, Alpesh
    Pandya, Himanshu A.
    Patel, Hitesh D.
    JOURNAL OF MOLECULAR STRUCTURE, 2019, 1181 : 383 - 402
  • [40] Photophysical study of 6-amino-3-methyl-4-(4-nitrophenyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile and estimation of ground-state and singlet excited-state dipole moments by solvatochromic approaches
    Kumari, Rekha
    Varghese, Anitha
    George, Louis
    Akshaya, K. B.
    JOURNAL OF MOLECULAR LIQUIDS, 2016, 222 : 828 - 835