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

Agnieszka Kudelko; Wojciech Zieliński

doi:10.1016/j.tet.2008.11.096

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

Agnieszka Kudelko
, Wojciech Zieliński

Katedra Technologii Chemicznej Organicznej i Petrochemii (RCH/RCH5)

Silesian University of Technology

Wyniki badań: Wkład do czasopisma › Artykuł › recenzja

21 Cytowania z bazy Scopus

Abstrakt

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.

Język oryginału	angielski
Strony (od–do)	1200-1206
Liczba stron	7
Czasopismo	Tetrahedron
Tom	65
Numer wydania	6
Identyfikatory DOI	https://doi.org/10.1016/j.tet.2008.11.096
Status publikacji	Opublikowano - 7 lut 2009

Obszary tematyczne ASJC Scopus

Biochemia
Odkrywanie leków
Chemia organiczna

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10.1016/j.tet.2008.11.096

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Cytowanie

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

abstract = "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.",

keywords = "2-Aminomethyl-1,3,4-oxadiazole, Enantiomers, Phenylglycine hydrazides, Protecting group, Racemization",

author = "Agnieszka Kudelko and Wojciech Zieli{\'n}ski",

year = "2009",

month = feb,

day = "7",

doi = "10.1016/j.tet.2008.11.096",

language = "English",

volume = "65",

pages = "1200--1206",

journal = "Tetrahedron",

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TY - JOUR

T1 - An efficient synthesis of new 2-aminomethyl-1,3,4-oxadiazoles from enantiomeric phenylglycine hydrazides

AU - Kudelko, Agnieszka

AU - Zieliński, Wojciech

PY - 2009/2/7

Y1 - 2009/2/7

N2 - 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.

AB - 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.

KW - 2-Aminomethyl-1,3,4-oxadiazole

KW - Enantiomers

KW - Phenylglycine hydrazides

KW - Protecting group

KW - Racemization

UR - https://www.scopus.com/pages/publications/58149151068

U2 - 10.1016/j.tet.2008.11.096

DO - 10.1016/j.tet.2008.11.096

M3 - Article

AN - SCOPUS:58149151068

SN - 0040-4020

VL - 65

SP - 1200

EP - 1206

JO - Tetrahedron

JF - Tetrahedron

IS - 6

ER -

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

Abstrakt

Obszary tematyczne ASJC Scopus

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