New synthetic strategy for Friedlander condensation of 4-amino-2-oxo-2H-chromene-3-carbaldehyde by heterogeneous catalysis

被引:6
|
作者
Jadhav, Ghanshyam R. [1 ]
Medhane, Vijay J. [1 ,2 ]
Deshmukh, Dattatray G. [1 ]
Gaikwad, Sharad S. [1 ]
机构
[1] SP Pune Univ, Post Grad Dept Chem, Chem Res Ctr, KTHM Coll, Gangapur Rd, Nasik 422002, Maharashtra, India
[2] SP Pune Univ, Dept Chem, SVKT Coll, Deolali Camp, Nasik, India
关键词
POLYSUBSTITUTED QUINOLINES; 3-COMPONENT SYNTHESIS; HIGHLY EFFICIENT; ONE-STEP; CAMPTOTHECIN; ACID; 1,8-NAPHTHYRIDINES; NANOPARTICLES; DERIVATIVES; ANNULATION;
D O I
10.1002/jhet.4308
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chromenopyridines are an important class of compound because of their diverse biological activities. In the present work, we have developed convenient route for the synthesis of chromeno[4,3-b] pyridine derivatives (3a-e, 5a-e, and 7a-d) by Friedlander condensation of 4-amino-2-oxo-2H-chromene-3-carbaldehyde with various active methylene compounds. We have used mixed metal oxide catalyst such as nanomaterial Zinc titanate. The reaction was carried out for various solvent systems, also we have altered the concentration of the catalyst. The 2-propanol/water solvent system and 5 mol% catalyst concentration are best as far as yield and rate of reaction are concerned. The structures of the synthesized compounds were confirmed by H-1 NMR, C-13 NMR, mass spectra, and elemental analysis.
引用
收藏
页码:1775 / 1783
页数:9
相关论文
共 50 条
  • [41] 2-Amino-4-(nitroalkyl)-4H-chromene-3-carbonitriles as New Cytotoxic Agents
    Zonouzi, Afsaneh
    Mirzazadeh, Roghieh
    Safavi, Maliheh
    Ardestani, Sussan Kabudanian
    Emami, Saeed
    Foroumadi, Alireza
    IRANIAN JOURNAL OF PHARMACEUTICAL RESEARCH, 2013, 12 (04): : 679 - 685
  • [42] 4-Oxo-N-phenyl-4H-chromene-2-carboxamide and of a new polymorph of 7-methoxy-4-oxo-N-p-tolyl-4H-chromene-2-carboxamide and its hemihydrate
    Reis, Joana
    Gaspar, Alexandra
    Borges, Fernanda
    Gomes, Ligia R.
    Low, John Nicolson
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2013, 69 : 1527 - +
  • [43] 7-Diethylamino-2-oxo-2H-chromene-3-carbohydrazide
    Zhang, Li-Jun
    Yin, Bing-Zhu
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O1107 - U266
  • [44] Photo- and ionochromic indoline spiropyrans based on 7,8-dihydroxy-4-methyl-2-oxo-2H-chromene-6-carbaldehyde
    Nikolaeva, O. G.
    Kostyrina, O. Yu.
    Shepelenko, E. N.
    Tsukanov, A. V.
    Metelitsa, A. V.
    Borodkin, G. S.
    Dubonosov, A. D.
    Bren', V. A.
    Minkin, V. I.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 47 (09) : 1370 - 1374
  • [45] Photo- and ionochromic indoline spiropyrans based on 7,8-dihydroxy-4-methyl-2-oxo-2H-chromene-6-carbaldehyde
    O. G. Nikolaeva
    O. Yu. Kostyrina
    E. N. Shepelenko
    A. V. Tsukanov
    A. V. Metelitsa
    G. S. Borodkin
    A. D. Dubonosov
    V. A. Bren’
    V. I. Minkin
    Russian Journal of Organic Chemistry, 2011, 47 : 1370 - 1374
  • [46] 4 '-Cyanobiphenyl-4-yl 7-diethylamino-2-oxo-2H-chromene-3-carboxylate
    Sreenivasa, S.
    Srinivasa, H. T.
    Palakshamurthy, B. S.
    Kumar, Vijith
    Devarajegowda, H. C.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O266 - +
  • [47] 3-methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid
    Hong, Zhi
    Jiang, Hua-Jiang
    Zhuang, Yu-Guo
    Guo, Hai-Chang
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O857 - U1868
  • [48] Diastereoselective multi-component tandem condensation: synthesis of 2-amino-4-(2-furanone)-4H-chromene-3-carbonitriles
    Gupta, Vijay
    Sahu, Debashish
    Jain, Shailja
    Vanka, Kumar
    Singh, Ravi P.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (39) : 8853 - 8857
  • [49] Synthesis of New Substituted 2-amino-4H-benzo[h]chromene-3-carbonitrile Derivatives
    Liu, Ju
    Shi, Jian Tao
    Hao, Xue Chen
    Liu, Yu Tong
    Ding, Shi
    Wang, Yang
    Chen, Ye
    JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2019, 41 (05): : 888 - 892
  • [50] 4-(Decyloxy) phenyl 2-oxo-7-trifluoromethyl-2H-chromene-3-carboxylate
    Palakshamurthy, B. S.
    Devarajegowda, H. C.
    Srinivasa, H. T.
    Sreenivasa, S.
    Vijithkumar
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O621 - +