Synthesis of novel 1-[(1-ethoxymethylene)amino]imidazol-5(4H)-ones and 1,2,4-triazin-6(5H)-ones from optically active α-aminocarboxylic acid hydrazides

Agnieszka Kudelko; Wojciech Zieliński; Karolina Jasiak

doi:10.1016/j.tetlet.2013.06.052

Synthesis of novel 1-[(1-ethoxymethylene)amino]imidazol-5(4H)-ones and 1,2,4-triazin-6(5H)-ones from optically active α-aminocarboxylic acid hydrazides

Agnieszka Kudelko
, Wojciech Zieliński
, Karolina Jasiak

Department of Chemical Organic Technology and Petrochemistry (RCH/RCH5)

Silesian University of Technology

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

Abstract

New derivatives of 1-[(1-ethoxymethylene)amino]imidazol-5(4H)-one and 1,2,4-triazin-6(5H)-one were synthesized via reactions of optically active α-aminocarboxylic acid hydrazides and triethyl orthoesters in xylene. The factors influencing the formation of the unexpected five-membered products and attempts to elucidate the mechanism are discussed.

Original language	English
Pages (from-to)	4637-4640
Number of pages	4
Journal	Tetrahedron Letters
Volume	54
Issue number	35
DOIs	https://doi.org/10.1016/j.tetlet.2013.06.052
Publication status	Published - 28 Aug 2013

Keywords

Cyclization
Heterocycles
Racemization
α-Aminocarboxylic acid hydrazide

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2013.06.052

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title = "Synthesis of novel 1-[(1-ethoxymethylene)amino]imidazol-5(4H)-ones and 1,2,4-triazin-6(5H)-ones from optically active α-aminocarboxylic acid hydrazides",

abstract = "New derivatives of 1-[(1-ethoxymethylene)amino]imidazol-5(4H)-one and 1,2,4-triazin-6(5H)-one were synthesized via reactions of optically active α-aminocarboxylic acid hydrazides and triethyl orthoesters in xylene. The factors influencing the formation of the unexpected five-membered products and attempts to elucidate the mechanism are discussed.",

keywords = "Cyclization, Heterocycles, Racemization, α-Aminocarboxylic acid hydrazide",

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

year = "2013",

month = aug,

day = "28",

doi = "10.1016/j.tetlet.2013.06.052",

language = "English",

volume = "54",

pages = "4637--4640",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Synthesis of novel 1-[(1-ethoxymethylene)amino]imidazol-5(4H)-ones and 1,2,4-triazin-6(5H)-ones from optically active α-aminocarboxylic acid hydrazides

AU - Kudelko, Agnieszka

AU - Zieliński, Wojciech

AU - Jasiak, Karolina

PY - 2013/8/28

Y1 - 2013/8/28

N2 - New derivatives of 1-[(1-ethoxymethylene)amino]imidazol-5(4H)-one and 1,2,4-triazin-6(5H)-one were synthesized via reactions of optically active α-aminocarboxylic acid hydrazides and triethyl orthoesters in xylene. The factors influencing the formation of the unexpected five-membered products and attempts to elucidate the mechanism are discussed.

AB - New derivatives of 1-[(1-ethoxymethylene)amino]imidazol-5(4H)-one and 1,2,4-triazin-6(5H)-one were synthesized via reactions of optically active α-aminocarboxylic acid hydrazides and triethyl orthoesters in xylene. The factors influencing the formation of the unexpected five-membered products and attempts to elucidate the mechanism are discussed.

KW - Cyclization

KW - Heterocycles

KW - Racemization

KW - α-Aminocarboxylic acid hydrazide

UR - https://www.scopus.com/pages/publications/84880848167

U2 - 10.1016/j.tetlet.2013.06.052

DO - 10.1016/j.tetlet.2013.06.052

M3 - Article

AN - SCOPUS:84880848167

SN - 0040-4039

VL - 54

SP - 4637

EP - 4640

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 35

ER -

Synthesis of novel 1-[(1-ethoxymethylene)amino]imidazol-5(4H)-ones and 1,2,4-triazin-6(5H)-ones from optically active α-aminocarboxylic acid hydrazides

Abstract

Keywords

ASJC Scopus subject areas

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