Heterocyclic Synthesis with Azides. I. The Reaction of Hydrazoic Acid with Ethoxymethylenemalonate

Augustine Donkor; Rolf H Prager; Malcolm J Thompson

doi:10.1071/CH9921571

Heterocyclic Synthesis with Azides. I. The Reaction of Hydrazoic Acid with Ethoxymethylenemalonate

Augustine Donkor
, Rolf H Prager
, Malcolm J Thompson

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

2 Citations (Scopus)

Abstract

Reaction of diethyl ethoxymethylenemalonate with sodium azide in trifluoroacetic acid at 20' gives ethyl 5-ethoxyisoxazole-4-carboxylate (67%), diethyl cyanomalonate (21%) and diethyl ethoxyaminomethylenemalonate (5%). The last compound and its tautomer are converted into ethyl l-ethoxy-3-oxo-2, 3-dihydro-1H-pyrazole-4-carboxylatTeh.e product stuctures have been confirmed by synthesis or degradation.

Original language	English
Pages (from-to)	1571-1576
Number of pages	6
Journal	Australian Journal of Chemistry
Volume	45
Issue number	10
DOIs	https://doi.org/10.1071/CH9921571
Publication status	Published - 1992

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title = "Heterocyclic Synthesis with Azides. I. The Reaction of Hydrazoic Acid with Ethoxymethylenemalonate",

abstract = "Reaction of diethyl ethoxymethylenemalonate with sodium azide in trifluoroacetic acid at 20' gives ethyl 5-ethoxyisoxazole-4-carboxylate (67\%), diethyl cyanomalonate (21\%) and diethyl ethoxyaminomethylenemalonate (5\%). The last compound and its tautomer are converted into ethyl l-ethoxy-3-oxo-2, 3-dihydro-1H-pyrazole-4-carboxylatTeh.e product stuctures have been confirmed by synthesis or degradation.",

author = "Augustine Donkor and Prager, \{Rolf H\} and Thompson, \{Malcolm J\}",

year = "1992",

doi = "10.1071/CH9921571",

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journal = "Australian Journal of Chemistry",

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T1 - Heterocyclic Synthesis with Azides. I. The Reaction of Hydrazoic Acid with Ethoxymethylenemalonate

AU - Donkor, Augustine

AU - Prager, Rolf H

AU - Thompson, Malcolm J

PY - 1992

Y1 - 1992

N2 - Reaction of diethyl ethoxymethylenemalonate with sodium azide in trifluoroacetic acid at 20' gives ethyl 5-ethoxyisoxazole-4-carboxylate (67%), diethyl cyanomalonate (21%) and diethyl ethoxyaminomethylenemalonate (5%). The last compound and its tautomer are converted into ethyl l-ethoxy-3-oxo-2, 3-dihydro-1H-pyrazole-4-carboxylatTeh.e product stuctures have been confirmed by synthesis or degradation.

AB - Reaction of diethyl ethoxymethylenemalonate with sodium azide in trifluoroacetic acid at 20' gives ethyl 5-ethoxyisoxazole-4-carboxylate (67%), diethyl cyanomalonate (21%) and diethyl ethoxyaminomethylenemalonate (5%). The last compound and its tautomer are converted into ethyl l-ethoxy-3-oxo-2, 3-dihydro-1H-pyrazole-4-carboxylatTeh.e product stuctures have been confirmed by synthesis or degradation.

UR - https://www.scopus.com/pages/publications/84970601878

U2 - 10.1071/CH9921571

DO - 10.1071/CH9921571

M3 - Article

AN - SCOPUS:84970601878

SN - 0004-9425

VL - 45

SP - 1571

EP - 1576

JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

IS - 10

ER -

Heterocyclic Synthesis with Azides. I. The Reaction of Hydrazoic Acid with Ethoxymethylenemalonate

Abstract

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