76885-39-7

Upstream product

• 3034-53-5 2-bromo-1,3-thiazole 
• 100-46-9 benzylamine 
• 623-47-2 propynoic acid ethyl ester 

Relevant academic research and scientific papers

Regioselective Aluminum Chloride Catalyzed Reactions of Unsaturated Electtrophiles with Thiazoles

Aluminum chloride promotes reactions of α,β-unsaturated esters and nitriles with 1,3-thiazoles to give 1:1 and 2:1 adducts, the nature and distribution of which depend on the substituent R at C2 of the heterocycle and the nuleophile QN employed as a quencher of the reaction mixture.With 2-bromothiazole, ethyl propiolate, and dimethyl acetylenedicarboxylate give substituted (E)- and (Z)-N-vinylthiazolin-2-ones (QN, aqueous sodium bicarbonate) and 2-imino-N-vinylthiazolines (QN, benzylamine), while ethyl acrylate and acrylonitrile afford substituted N-propanoylthiazolin-2-ones (QN, aqueous sodium bicarbonate).With 1,3-thiazole and 2-ethylthiazole, ethyl propiolate gives (QN, aqueous sodium bicarbonate) N-formyl- and N-propanoylthiazolines, respectively, together with 2:1 open-chain adducts containing 2 mol of acetylene and 1 mol of thiazole.A plausible scheme accounting for the formation of the observed products involves a regioselective attack by Cβ of the multiple bond of the ester or nitrile coordinated with AlCl3 on the nitrogen of the thiazole ring to give a zwitterion with allenic structure which by action of the QN undergoes C2-R (R = Br) or C2-S (R = H, C2H5) bond fission and forms the observed products.

Regioselective Aluminium Chloride-catalysed Reactions of Acetylenic Esters with 2-Bromothiazole

Ethyl propiolate and dimethyl acetylenedicarboxylate activated by AlCl3 react with 2-bromothiazole to give, after quenching with aqueous NaHCO3 or PhCH2NH2, N-vinylthiazolin-2-ones and 2-benzylimino-N-vinylthiazolines respectively.