Synthesis of Novel Bis(thiazolylchromen‐2‐one) Derivatives Linked to Alkyl Spacer via Phenoxy Group

Abstract

A novel series of bis(thiazolylchromen‐2‐one) derivatives 8 were prepared in good yields by the reaction of the appropriate bis(α‐bromoketones) 7 with 2‐(1‐(2‐oxo‐2H‐chromen‐3‐yl)ethylidene) hydrazinecarbothioamide (6) in refluxing EtOH in the presence of few drops of TEA. Some other isomeric derivatives of bis(thiazolylchromen‐2‐one) 11 and 13 were also successfully obtained by the reaction of bromoacetylcoumarin 9 with the corresponding bis(ethan‐1‐yl‐1‐ylidene))bis(hydrazinecarbothioamides) 10 and 12. The structures of the new compounds were established based on elemental analyses as well as spectral data.

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

“…Numerous protocols for the synthesis of thiazolyl-linker-thiazole compounds have been reported in the literature, most of them being based on the Hantzsch condensation reaction. The reaction can occur in a single step, when the two thiazole rings are formed simultaneously, using starting compounds such as bis-thiosemicarbazones, 2,5-dithiobiurea, bis-hydrazonoyl halides, or dihalo diketones, or in two steps when the two thiazole rings are formed successively [ 94 , 95 , 96 , 97 , 98 , 99 ].…”

3-(Bromoacetyl)coumarins: unraveling their synthesis, chemistry, and applications

“…94,128 The bis(thiazole-4,2-diyl)bis(2H-chromen-2-ones) 103 and 104 were obtained via one-pot cyclisation reaction of bis(hydrazinecarbothioamides) 102 with 3-(bromoacetyl)coumarin 1 (Scheme 44). 94,129 Cyclization reaction of 3-(bromoacetyl)coumarin 1 with thiosemicarbazides 105 in the presence of a catalytic amount of trimethylamine in ethanol yielded thiazolylcoumarin derivatives 106 (Scheme 45). 130 Reuxing of 3-(bromoacetyl)coumarin 1 and coumarinothiosemicarbazides 107a-m in methanol containing drops of acetic acid as catalyst gave bis-coumarin-iminothiazole hybrids 108a-m in good yields (Scheme 46).…”

Novel Scaffolds Based on Bis-thiazole Connected to Quinoxaline or Thienothiophene through 2-Phenoxy-N-arylacetamide Groups as New Hybrid Molecules: Synthesis, Antibacterial Activity, and Molecular Docking Investigations

“…The pharmacophore scaffolds of several compounds are combined to create hybrid molecules. In this regard, anticancer drugs that are safer and more effective than those presently on the market may benefit from hybridization. , In light of these findings, as well as our continuing interest in the synthesis of heterocycles − and their bis­(heterocycles), − we sought to incorporate N -arylacetamide units into the backbone of thiazole to obtain a novel series of bis-thiazole derivatives linked through biologically active quinoxaline or thienothiophene cores using a “hybrid conjugation of bioactive ligands” approach. Our synthetic strategy employs 2-(4-(1-(2-carbamothioylhydrazineylidene)­ethyl)­phenoxy)- N -(aryl)­acetamides, 2-(4-(2-bromoacetyl)­phenoxy)- N -(aryl)­acetamides, bis­(4,1-phenylene)­bis­(2-bromoethan-1-ones) 7 , bis­(α-bromoketone), and bis­(thiosemicarbazone) as precursors (Figure ).…”