Regioselective synthesis of methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates as new amino acid-like building blocks

A convenient and efficient synthesis of novel achiral and chiral heterocyclic amino acid-like building blocks was developed. Regioisomeric methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates were prepared by the reaction of β-enamino ketoesters (including azetidine, pyrrolidine or piperidine enamines) with hydroxylamine hydrochloride. Unambiguous structural assignments were based on chiral HPLC analysis, 1H, 13C, and 15N NMR spectroscopy, HRMS, and single-crystal X-ray diffraction data.

Green and efficient synthesis of 1, 2, 4-Triazolidine-3-thiones using guanidine hydrochloride as a recyclable catalyst under the aqueous condition

A rapid and highly efficient methodology for the synthesis of 1, 2, 4-Triazolidine-3-thiones derivatives has been developed in the presence of a catalytic amount of guanidine hydrochloride using water as a solvent. The reaction of thiosemicarbazide with different aryl aldehydes resulted in the formation of title compounds in good yields (85% -95%) with a convenient reaction time (20-30 min). The key advantages of this approach are shorter reaction time, energy efficiency, easy work-up procedure, and wide substrate scope tolerance. Further, the catalyst was recycled without significant loss of its catalytic activity

Efficient synthesis of ethyl 2-(oxazolin-2-yl)alkanoates via ethoxycarbonylketene-induced electrophilic ring expansion of aziridines

Alkyl 2-diazo-3-oxoalkanoates generate alkoxycarbonylketenes, which undergo an electrophilic ring expansion with aziridines to afford alkyl 2-(oxazolin-2-yl)alkanoates in good to excellent yields under microwave heating. The method is a convenient and clean reaction without any activators and catalysts and can be also applied in the synthesis of 2-(oxazolin-2-yl)alkanamides and 1-(oxazolin-2-yl)alkylphosphonates.