An efficient synthesis of new 2-aminomethyl-1,3,4-oxadiazoles from enantiomeric phenylglycine hydrazides

作者：Kudelko Agnieszka^*; Zielinski Wojciech

来源：Tetrahedron, 2009, 65(6): 1200-1206.

DOI：10.1016/j.tet.2008.11.096

• 2-Aminomethyl-1,3,4-oxadiazole
• Phenylglycine hydrazides
• Enantiomers
• Protecting group
• Racemization

New derivatives of 2-aminomethyl-1,3,4-oxadiazole were synthesized in the reactions of N-protected phenylglycine hydrazides and triethyl orthoesters (orthoformate, orthoacetate, orthopropionate, orthobenzoate) in the presence of glacial acetic acid. Studies on the cleavage reactions of the acid-sensitive N-BOC and N-Ac 1,3,4-oxadiazoles are presented. Spectral characteristics of the Compounds and attempts to elucidate the racemization phenomenon observed in products are also discussed.

• 出版日期2009-2-7