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

被引：22
|
作者：
Kudelko, Agnieszka [1 ]
Zielinski, Wojciech [1 ]
机构：
[1] Silesian Tech Univ, Dept Chem Organ Technol & Petrochem, PL-44101 Gliwice, Poland
来源：
TETRAHEDRON | 2009年 / 65卷 / 06期
关键词：
2-Aminomethyl-1,3,4-oxadiazole; Phenylglycine hydrazides; Enantiomers; Protecting group; Racemization; ONE-POT SYNTHESIS; ALPHA-AMINO-ACIDS; 2,5-DISUBSTITUTED 1,3,4-OXADIAZOLES; SUBSTITUTED 1,3,4-OXADIAZOLES; SELECTIVE REMOVAL; DEPROTECTION; REAGENT; MILD;
D O I：
10.1016/j.tet.2008.11.096
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1200 / 1206
页数：7
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