Synthesis of ν-triazole derivatives from anomeric sugar diazides

J. Kovács, I. Pintér, M. Kajtár-Peredy, G. Argay, A. Kálmán, Gérard Descotes, Jean Pierre Praly

Research output: Article

7 Citations (Scopus)

Abstract

Staudinger reaction of acetylated glycopyranosylidene 1,1-diazides led to resonance-stabilized iminophosphoranes (phosphinimines) of 6,7-dihydro[3,4-d]-1,2,3-triazole. This unprecedented transformation involves β-elimination of acetic acid and cycloaddition of azide anion to the resulting C-2 double bond. Transformation of the new fused heterocyclic iminophosphoranes on treatment with aqueous ethanolic ammonia gives carboxamidine derivatives of ν-triazole bearing a chiral trihydroxypropyl side-chain. Crystal structure of 5-(d-erythro-1',2',3'-trihydroxypropyl)-1,2,3-triazole-4-carboxamidine was established by X-ray crystallography. Copyright (C) 1999 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)112-120
Number of pages9
JournalCarbohydrate Research
Volume316
Issue number1-4
DOIs
Publication statusPublished - márc. 15 1999

Fingerprint

Triazoles
Sugars
Derivatives
Bearings (structural)
Azides
Cycloaddition
X ray crystallography
X Ray Crystallography
Cycloaddition Reaction
Ammonia
Acetic Acid
Anions
Crystal structure

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Synthesis of ν-triazole derivatives from anomeric sugar diazides. / Kovács, J.; Pintér, I.; Kajtár-Peredy, M.; Argay, G.; Kálmán, A.; Descotes, Gérard; Praly, Jean Pierre.

In: Carbohydrate Research, Vol. 316, No. 1-4, 15.03.1999, p. 112-120.

Research output: Article

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AU - Kovács, J.

AU - Pintér, I.

AU - Kajtár-Peredy, M.

AU - Argay, G.

AU - Kálmán, A.

AU - Descotes, Gérard

AU - Praly, Jean Pierre

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AB - Staudinger reaction of acetylated glycopyranosylidene 1,1-diazides led to resonance-stabilized iminophosphoranes (phosphinimines) of 6,7-dihydro[3,4-d]-1,2,3-triazole. This unprecedented transformation involves β-elimination of acetic acid and cycloaddition of azide anion to the resulting C-2 double bond. Transformation of the new fused heterocyclic iminophosphoranes on treatment with aqueous ethanolic ammonia gives carboxamidine derivatives of ν-triazole bearing a chiral trihydroxypropyl side-chain. Crystal structure of 5-(d-erythro-1',2',3'-trihydroxypropyl)-1,2,3-triazole-4-carboxamidine was established by X-ray crystallography. Copyright (C) 1999 Elsevier Science Ltd.

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KW - Glycopyranosylidene 1,1-diazides

KW - Iminophosphoranes (phosphinimines)

KW - Pyrano[3,4-D]-1,2,3-triazole

KW - Staudinger reaction

KW - X-ray structure

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