Part -IV: Utilities of active methylene compounds and heterocycles bearing active methyl or having an active methine in the synthesis of triazoles, pyridazines, triazines and diazepines

被引:3
作者
Abdel-Megid, Mohamed [1 ,2 ]
机构
[1] Ain Shams Univ, Dept Chem, Fac Educ, Cairo, Egypt
[2] Shaqra Univ, Coll Sci & Humanities Hurymmila, Shaqraa, Saudi Arabia
关键词
Active methylene; triazoles; pyridazines; triazines; diazepines; biological importance;
D O I
10.1080/00397911.2020.1865404
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Common and novel synthesized active methylene compounds as well as heterocycles bearing active methyl or having an active methine were used in the syntheses of a wide variety of substituted and fused five-, six- and seven-membered nitrogenous heterocyclic systems of interesting medical and pharmaceutical importance such as triazoles, pyridazines, triazines, and diazepines. Carbothiosemicarbazides, carbothiohydrazones and 2-hydrazinoazaherterocycles were used as suitable starting materials for triazole formation. The preparation of tetrazoles showed a valence ring-chain tautomerism. The key starting materials for the synthesis of pyridazines were acetohydrazide derivative, activated enones, enaminones, and aryl hydrazones. The reaction of 2-chloro or 2-hydrazinoazaheterocycles and thiocarbohydrazones with different reagents under suitable reaction conditions led to the formation of triazines. Diazepines were obtained via treatment of enones with 1,2-diamino derivatives. Also, the antimicrobial activities of some selected synthesized heterocyclic compounds were reported.
引用
收藏
页码:971 / 996
页数:26
相关论文
共 42 条
[31]  
Mohamed O.F., 2012, EUR J CHEM, V3, P273, DOI [10.5155/eurjchem.3.3.273-278.605, DOI 10.5155/EURJCHEM.3.3.273-278.605]
[32]   Synthesis of Pyrido-annelated Diazepines, Oxazepines and Thiazepines [J].
Muylaert, Koen ;
Jatczak, Martyna ;
Mangelinckx, Sven ;
Stevens, Christian V. .
CURRENT MEDICINAL CHEMISTRY, 2016, 23 (42) :4784-4823
[33]  
NAKKA M, 2014, SYNTHESIS, V47
[34]   SCREENING METHODS FOR NATURAL-PRODUCTS WITH ANTIMICROBIAL ACTIVITY - A REVIEW OF THE LITERATURE [J].
RIOS, JL ;
RECIO, MC ;
VILLAR, A .
JOURNAL OF ETHNOPHARMACOLOGY, 1988, 23 (2-3) :127-149
[35]  
Seada M., 1992, ASIAN J CHEM, V4, P544
[36]  
Seada M., 2017, PHARM CHEM, V9, P86
[37]   Microwave-Assisted Catalyst-Free Synthesis of Substituted 1,2,4-Triazoles [J].
Shelke, Ganesh M. ;
Rao, V. Kameswara ;
Jha, Mukund ;
Cameron, T. Stan ;
Kumar, Anil .
SYNLETT, 2015, 26 (03) :404-407
[38]   Multicomponent Synthesis of 1-Aryl 1,2,4-Triazoles [J].
Tam, Annie ;
Armstrong, Ian S. ;
La Cruz, Thomas E. .
ORGANIC LETTERS, 2013, 15 (14) :3586-3589
[39]  
Verma A., 2013, J. Chem, V2013
[40]  
WANG LY, 2011, SYNLETT, V2011