Synthesis and characterization of some novel bis‐thiazoles

Abstract

The bis‐thiosemicarbazone derivative 3 was prepared and reacted with N‐aryl‐2‐oxopropane hydrazonoyl chloride 4a‐g and ethyl (N‐arylhydrazono)chloroacetate 7a‐e in absolute ethanol in the presence of triethylamine at reflux afforded a new series of thiazoles 6a‐g and 9a‐e, respectively. Also, thiosemicarbazone derivative 3 was reacted with N′‐phenylbenzohydrazonoyl chloride 10 to give the respective bis‐thiadiazole derivative 12. Moreover, the reaction of 3 with a number of haloketones and haloesters furnished the respective bis‐thiazole derivatives 14, 16, 18, and 20. The mechanisms that account for formation of products 6, 9, and 12 were discussed. Also, the molecular structure of the synthesized compounds was illustrated by spectroscopic and elemental analysis.

An Overview of the Synthesis and Antimicrobial, Antiprotozoal, and Antitumor Activity of Thiazole and Bisthiazole Derivatives

“…Mahmoud et al [ 101 ] developed a new synthetic method starting from a bis-thiosemicarbazone derivative, which contains a voluminous linkage. The compound reacted with two equivalents of various hydrazonoyl chlorides, in the presence of triethylamine, in refluxing dioxane or α-halocarbonyl derivatives, in refluxing ethanol, leading to the formation of novel bisthiazole derivatives ( Scheme 24 ).…”

“…Gomha et al [100] synthesized bisthiazole derivatives by the condensation reaction between various thiosemicarbazones and bis-hydrazonoyl chlorides, in the presence of triethylamine, under reflux conditions in dioxane, for 4-8 h (Scheme 23). Mahmoud et al [101] developed a new synthetic method starting from a bis-thiosemicarbazone derivative, which contains a voluminous linkage. The compound reacted with two equivalents of various hydrazonoyl chlorides, in the presence of triethylamine, in refluxing dioxane or α-halocarbonyl derivatives, in refluxing ethanol, leading to the formation of novel bisthiazole derivatives (Scheme 24).…”

Cross-Linked Chitosan/Multi-Walled Carbon Nanotubes Composite as Ecofriendly Biocatalyst for Synthesis of Some Novel Benzil Bis-Thiazoles

“…Continuing our work on bis-heterocycle synthesis [31][32][33][34][35], the starting compound 2,2′-(1,2-diphenylethane-1,2-diylidene)bis(hydrazinecarbothioamide) 2 was obtained via reaction of benzil 1 with thiosemicarbazide in a molar ratio of 1:2 in refluxing EtOH/drops HCl for 3 h using a published procedure [36] (Scheme 1). The second thermal degradation step was sharp and started at 270 • C. The weight losses of chitosan, CLCS and CLCS/MWCNTs composite at 500 • C were 65.46%, 57.95% and 53.29%, respectively (Table 1).…”

Facile synthesis of novel heterocyclic compounds based on pyridine moiety with pharmaceutical activities

“…calcd. for C 25 3.23 | N-(3,5-dicyano-4-phenyl-6-(phenylamino)pyridin-2-yl) acetamide (23) A mixture of pyridine derivative 1 (0.01 mol, 3.11 g) and freshly distilled acetic anhydride (10 mL) was heated under reflux for 3 hours. The solid that deposited after distilling the excess solvent and poured on ice/water was collected and recrystallized from benzene to give 23.…”

“…Besides, they are important and useful intermediates in preparing a variety of heterocyclic compounds [12,21] . In extension of our previous work [22][23][24][25][26][27] , 2-amino-4-phenyl-6-(phenylamino) pyridine-3,-5-dicarbonitrile will be utilized as a substrate for the synthesis of different heterocyclic derivatives, and their pharmaceutical behavior as anticancer agent will be studied.…”