P Mary Antony, Chakravarthy A S Jeevan, Ila Hiriyakkanavar
New Chemistry Unit, Jawaharlal Nehru Centre for Advanced Scientific Research, Jakkur, Bangalore 560064, India.
J Org Chem. 2024 Apr 5;89(7):4453-4460. doi: 10.1021/acs.joc.3c02591. Epub 2024 Mar 26.
A facile transition-metal-free synthesis of 3,5-bis(het)aryl/arylaminothiadiazoles has been reported. The overall protocol involves base-mediated tandem thioacylation of amidines with dithioesters or aryl isothiocyanates in DMF solvent and subsequent in situ intramolecular dehydrogenative N-S bond formation of thioacylamidine intermediates under an inert atmosphere. A probable mechanism involving a carbamoyl anion, generated by deprotonation of DMF, acting as a radical initiator has been suggested.
据报道，已实现了一种简便的无过渡金属合成3,5-双（杂）芳基/芳基氨基噻二唑的方法。整个方案包括在DMF溶剂中，碱介导的脒与二硫代酯或芳基异硫氰酸酯的串联硫酰化反应，以及随后在惰性气氛下，硫酰脒中间体原位分子内脱氢形成N-S键。有人提出了一种可能的机理，即由DMF去质子化产生的氨基甲酰阴离子作为自由基引发剂。
