Volume 22, Issue 39
Heterocyclic Compounds
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ChemInform Abstract: 1,2,3-Triazoles from Z-β-(Formyloxy)vinyl Azides and Triethyl Phosphite.

S. V. D'ANDREA

S. V. D'ANDREA

Dep. Chem. Biochem., Univ., Notre Dame, IN 46556, USA

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A. GHOSH

A. GHOSH

Dep. Chem. Biochem., Univ., Notre Dame, IN 46556, USA

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W. WANG

W. WANG

Dep. Chem. Biochem., Univ., Notre Dame, IN 46556, USA

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J. P. FREEMAN

J. P. FREEMAN

Dep. Chem. Biochem., Univ., Notre Dame, IN 46556, USA

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J. SZMUSZKOVICZ

J. SZMUSZKOVICZ

Dep. Chem. Biochem., Univ., Notre Dame, IN 46556, USA

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First published: October 1, 1991

Abstract

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ChemInform Abstract

Bromination of the dihydrophenalenone (I) followed by reaction with sodium azide (II) yields the α-azido ketone (III). This compound as well as the literature-known azido ketone (VIII) are metalated by means of sodium hexamethyldisilazide and then treated with the mixed anhydride (IV) to give the (formyloxy)vinyl azides (V) and (IX) respectively which cyclize upon reaction with triethyl phosphite, forming the triazoles (VI) or (X). The N-formyltriazole (VII) is obtained upon quenching the reaction of (V) with triethyl phosphite after a short time.

chemical structure image

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