Stereo- and regioselective synthesis of β-amino-β-tetrazolylvinylphosphonates

Nataly I. Svintsitskaya, Albina V. Dogadina, Galina L. Starova, Rostislav E. Trifonov

Research output

5 Citations (Scopus)

Abstract

Addition of 5-substituted tetrazoles to dimethyl [(N,N-diisopropylamino)ethynyl]phosphonate proceeds regio- and stereoselectively to yield (Z)[2-diisopropylamino-2-(tetrazolyl)vinyl]phosphonic acid dimethyl esters. The Z-configuration of the products was confirmed by H-1 NMR spectroscopy and single-crystal X-ray diffraction. The reactions occur via nucleophilic attack of tetrazole involving predominantly the N-1 atom of the tetrazole ring. (C) 2014 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)5381-5385
Number of pages5
JournalTetrahedron Letters
Volume55
Issue number39
DOIs
Publication statusPublished - 2014

Fingerprint

Tetrazoles
Organophosphonates
X-Ray Diffraction
Nuclear magnetic resonance spectroscopy
Esters
Magnetic Resonance Spectroscopy
Single crystals
X ray diffraction
Atoms
1H-tetrazole
phosphonic acid

Cite this

Svintsitskaya, Nataly I. ; Dogadina, Albina V. ; Starova, Galina L. ; Trifonov, Rostislav E. / Stereo- and regioselective synthesis of β-amino-β-tetrazolylvinylphosphonates. In: Tetrahedron Letters. 2014 ; Vol. 55, No. 39. pp. 5381-5385.
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abstract = "Addition of 5-substituted tetrazoles to dimethyl [(N,N-diisopropylamino)ethynyl]phosphonate proceeds regio- and stereoselectively to yield (Z)[2-diisopropylamino-2-(tetrazolyl)vinyl]phosphonic acid dimethyl esters. The Z-configuration of the products was confirmed by H-1 NMR spectroscopy and single-crystal X-ray diffraction. The reactions occur via nucleophilic attack of tetrazole involving predominantly the N-1 atom of the tetrazole ring. (C) 2014 Elsevier Ltd. All rights reserved.",
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Stereo- and regioselective synthesis of β-amino-β-tetrazolylvinylphosphonates. / Svintsitskaya, Nataly I.; Dogadina, Albina V.; Starova, Galina L.; Trifonov, Rostislav E.

In: Tetrahedron Letters, Vol. 55, No. 39, 2014, p. 5381-5385.

Research output

TY - JOUR

T1 - Stereo- and regioselective synthesis of β-amino-β-tetrazolylvinylphosphonates

AU - Svintsitskaya, Nataly I.

AU - Dogadina, Albina V.

AU - Starova, Galina L.

AU - Trifonov, Rostislav E.

PY - 2014

Y1 - 2014

N2 - Addition of 5-substituted tetrazoles to dimethyl [(N,N-diisopropylamino)ethynyl]phosphonate proceeds regio- and stereoselectively to yield (Z)[2-diisopropylamino-2-(tetrazolyl)vinyl]phosphonic acid dimethyl esters. The Z-configuration of the products was confirmed by H-1 NMR spectroscopy and single-crystal X-ray diffraction. The reactions occur via nucleophilic attack of tetrazole involving predominantly the N-1 atom of the tetrazole ring. (C) 2014 Elsevier Ltd. All rights reserved.

AB - Addition of 5-substituted tetrazoles to dimethyl [(N,N-diisopropylamino)ethynyl]phosphonate proceeds regio- and stereoselectively to yield (Z)[2-diisopropylamino-2-(tetrazolyl)vinyl]phosphonic acid dimethyl esters. The Z-configuration of the products was confirmed by H-1 NMR spectroscopy and single-crystal X-ray diffraction. The reactions occur via nucleophilic attack of tetrazole involving predominantly the N-1 atom of the tetrazole ring. (C) 2014 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.tetlet.2014.08.018

DO - 10.1016/j.tetlet.2014.08.018

M3 - Article

VL - 55

SP - 5381

EP - 5385

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 39

ER -