Synthesis, Reactions and Antibacterial Activity of 3-Acetyl[1,2,4]triazolo[3,4-a]isoquinoline Derivatives using Chitosan as Heterogeneous Catalyst under Microwave Irradiation

被引:27
作者
Hassaneen, Hamdi M. [1 ]
Hassaneen, Huwaida M. E. [1 ]
Mohammed, Yasmin Sh. [1 ]
Pagni, Richard M. [2 ]
机构
[1] Cairo Univ, Fac Sci, Dept Chem, Giza, Egypt
[2] Univ Tennessee, Dept Chem, Knoxville, TN 37996 USA
来源
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES | 2011年 / 66卷 / 03期
关键词
1,2,4]Triazolo[3,4-a]isoquinoline; Enaminones; Hydrazinolysis; Hydrazonoyl Chlorides; Cycloaddition Reaction; Chitosan; Hydroximoyl Chloride; HETEROCYCLES; REACTIVITY; 1-METHYLISOQUINOLINE; CHLORIDES;
D O I
10.5560/ZNB.2011.66b0299
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
3-Acetyl[1,2,4]tritizolo[3,4-a]isoquinolines were prepared using chitosan as a catalyst. These compounds were used to prepare a novel series of enaminones 5, and their reactions with hydrazonoyl halides 1 and 11 gave triazoloisoquinolines 8 and 13, respectively, with a carbonylpyrazole side chain. Hydrazinolysis of 8 and 13 gave the pyrazolopyridazines 10 and pyrazolopyridazinones 14. Reaction of 5 with hydroximoyl halides 15 led to triazoloisoquinoline 16 with a carbonylisoxazole side chain. Antibacterial effects of compounds 8 and 10 were studied.
引用
收藏
页码:299 / 310
页数:12
相关论文
共 45 条
[1]   Michael reactions of arylidenesulfonylacetonitriles.: A new route to polyfunctional benzo[a]quinolizines [J].
Abdallah, TA ;
Abdelhadi, HA ;
Hassaneen, HM ;
Hassaneen, HM .
MOLECULES, 2002, 7 (07) :540-548
[2]   Reactivity of 1-methylisoquinoline.: One pot synthesis of benzo[a]-quinolizine derivatives [J].
Abdallah, TA ;
Abdelhadi, HA ;
Ibrahim, AA ;
Hassaneen, HM .
SYNTHETIC COMMUNICATIONS, 2002, 32 (04) :581-589
[3]   Reactivity of 1-methylisoquinoline. Synthesis of 2-(1-isoquinolinemethylidene)-1,3,4-thiadiazole derivatives [J].
Abdallah, TA ;
Abdelhadi, HA ;
Hassaneen, HM .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2002, 177 (01) :59-66
[4]  
Abdelhadi HA, 1996, J CHEM RES-S, P292
[5]   HETEROCYCLES FROM NITRILE OXIDES - SYNTHESIS AND REACTIONS OF 2-THIENOYLHYDROXAMOYL CHLORIDE [J].
ABDELHAMID, AO ;
KHALIFA, FA ;
GHABRIAL, SS .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1988, 40 (1-2) :41-46
[6]  
ALMATAR HM, 2008, ARKIVOC, V16, P88
[7]   Synthesis of important new pyrrolo[3,4-c]pyrazoles and pyrazolyl-pyrrolines from heterocyclic β-ketonitriles [J].
Amer, Fathy Abdel-Kader ;
Hammouda, Metwally ;
El-Ahl, Abdel-Aziz Sayed ;
Abdel-Wahab, Bakr Fathy .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2007, 54 (06) :1543-1552
[8]   Microwave assisted solvent-, support- and catalyst-free synthesis of enaminones [J].
Andrade, Carlos Kleber Z. ;
Barreto, Angelica de Fatima S. ;
Silva, Wender A. .
ARKIVOC, 2008, :226-232
[9]  
[Anonymous], 1993, M7A3 NAT COMM CLIN L
[10]  
Awad EM, 2001, HELV CHIM ACTA, V84, P1172, DOI 10.1002/1522-2675(20010516)84:5<1172::AID-HLCA1172>3.0.CO