An efficient synthesis of 1,5-thiadiazepines and 1,5-benzodiazepines by microwave-assisted heterocyclization

被引:24
作者
Nagaraja, Gundibasappa K.
Vaidya, Vijayavittala P.
Rai, Koodamara Sheshappa
Mahadevan, Kittappa M. [1 ]
机构
[1] Kuvempu Univ, Dept Postgrad Studies & Res Chem, Shimoga 577451, Karnataka, India
[2] Univ Mysore, Sir MV PG Ctr, Dept PG Studies & Res Polymer Sci, Mandya, Karnataka, India
关键词
1-amino-2-mercapto-5-aryl-1,3,4-triazole; chalcones; heterocycliczation; microwave irradiation; o-phenylenediamine;
D O I
10.1080/10426500600864775
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A novel and efficient method for the synthesis of substituted thiazepines and diazepines has been developed. A simple one-pot reaction of chalcones 1a-f with 1-amino-2-mercapto-5-phenyl-1,3,4-triazole and o-phenylenediamine in the presence of a catalytic amount of sodium acetate under microwave irradiation gave 2-(3,8-diphenyl-7,8-dihydro[1,2,4]triazolo[3,4-b][1,3,4]thiadiazepin-6-yl)phenoles 2a-f and 2-(2-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-4-yl)phenoles 3a-f, respectively. The structure of all the synthesized compounds was elucidated on the basis of elemental analysis, IR, H-1 and C-13 NMR, and mass spectral data.
引用
收藏
页码:2797 / 2806
页数:10
相关论文
共 23 条
  • [21] ALUMINA-MEDIATED CLEAVAGE OF T-BUTYLDIMETHYLSILYL ETHERS
    VARMA, RS
    LAMTURE, JB
    VARMA, M
    [J]. TETRAHEDRON LETTERS, 1993, 34 (19) : 3029 - 3032
  • [22] Weiss K, 1989, Prog Clin Biol Res, V301, P353
  • [23] Amberlyst-15®:: a novel and recyclable reagent for the synthesis of 1,5-benzodiazepines in ionic liquids
    Yadav, JS
    Reddy, BVS
    Eshwaraiah, B
    Anuradha, K
    [J]. GREEN CHEMISTRY, 2002, 4 (06) : 592 - 594