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Synthesis and Antibacterial Evaluation of Some New Thiazole‐Based Polyheterocyclic Ring Systems
Author(s) -
AbdelLatif Ehab,
Almatari Altaf S.,
AbdElGhani Ghada E.
Publication year - 2019
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3577
Subject(s) - chemistry , thiazole , malononitrile , hydrazine (antidepressant) , ring (chemistry) , reagent , pyrimidine , pyridine , phenacyl bromide , iodide , pyrazole , thiourea , carbon disulfide , thioamide , methyl iodide , combinatorial chemistry , medicinal chemistry , organic chemistry , stereochemistry , catalysis , chromatography
2‐Cyanoacetamido‐thiazole ( 1 ) was employed as a key for the construction of 6‐cyano‐7‐oxo‐7 H ‐thiazolo[3,2‐ a ]pyrimidine ( 4 ) which underwent reaction with hydrazine, malononitrile, ethyl cyanoacetate, and/or various 1,3‐bi‐nuclophilic reagents furnished the corresponding tri‐heterocyclic and tetra‐heterocyclic ring systems 5 – 12 . In addition, the reactions of 1 with various types of arylidene‐malononitriles and/or ethyl 3‐aryl‐2‐cyanoacrylates yielded the corresponding 1‐thiazolyl‐pyridine derivatives 16 and 20 , respectively. Furthermore, treatment of the precursor 1 with carbon disulfide and methyl iodide afforded the ketene dithioacetal derivative 21 which cyclized upon heating with hydrazine and/or 2‐aminobenzimidazole into the corresponding derivatives of N ‐(thiazol‐2‐yl)‐1 H ‐pyrazole‐4‐carboxamide 22 and N ‐(thiazol‐2‐yl)benzimidazo[1,2‐ a ]‐pyrimidine‐3‐carboxamide 23 . The antibacterial properties of these thiazole‐based heterocycles were examined against panel of two bacterial strains.