On terminal alkynylcarbinols and derivatization thereof

Dymytrii Listunov; Valérie Maraval; Nathalie Saffon-Merceron; Sonia Mallet-Ladeira; Zoia Voitenko; Yulian Volovenko; Yves Génisson; Remi Chauvin

doi:10.17721/fujcV3I1P21-28

Authors

Dymytrii Listunov CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP44099, 31077 Toulouse Cedex 4 (France) UMR CNRS 5068, LSPCMIB, Université Paul Sabatier, 118 route de Narbonne, 31062 Toulouse Cedex 9, France Université de Toulouse, UPS, INPT, F-31077 Toulouse (France) Kiev National Taras Shevchenko University, 60 Volodymyrska St., 01033 Kiev, Ukraine
Valérie Maraval CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP44099, 31077 Toulouse Cedex 9, France Université de Toulouse, UPS, INPT, F-31077 Toulouse (France)
Nathalie Saffon-Merceron Université de Toulouse, UPS, Institut de Chimie de Toulouse ICT-FR-2599, 118 route de Narbonne, 31062 Toulouse Cedex 9
Sonia Mallet-Ladeira Université de Toulouse, UPS, Institut de Chimie de Toulouse ICT-FR-2599, 118 route de Narbonne, 31062 Toulouse Cedex 9
Zoia Voitenko Kiev National Taras Shevchenko University, 60 Volodymyrska St., 01033 Kiev, Ukraine
Yulian Volovenko Kiev National Taras Shevchenko University, 60 Volodymyrska St., 01033 Kiev, Ukraine
Yves Génisson Toulouse Cedex 4 (France) UMR CNRS 5068, LSPCMIB, Université Paul Sabatier, 118 route de Narbonne, 31062 Toulouse Cedex 9, France Université de Toulouse, UPS, INPT, F-31077 Toulouse (France)
Remi Chauvin CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP44099, 31077 Toulouse Cedex 9, France Université de Toulouse, UPS, INPT, F-31077 Toulouse (France)

DOI:

https://doi.org/10.17721/fujcV3I1P21-28

Keywords:

alkyne, alkynylcarbinol, pharmacophore, design, propargylic alcohol, 1, 2, 3-triazolylcarbinol

Abstract

The chemistry of three prototypes of secondary alkynylcarbinols (ACs), recently highlighted as challenging targets in anti-tumoral medicinal chemistry, is further documented by results on n-alkyl, alkynyl and alkenyl representatives. The N-naphthyl carbamate of an n-butyl-AC is thus characterized by X-ray crystallography. A novel dialkynylcarbinol (DAC) with synthetic potential is described, namely the highly dissymmetrical triisopropylsilyl-protected version of diethynylmethanol. The latter is shown to act as a dipolarophile in a selective Huisgen reaction with benzyl azide under CuAAC click conditions, giving an alkenyl-AC, where the alkene unsaturation is embedded in a 1,4-disubstituted 1,2,3-triazole ring, as confirmed by X-ray crystallography.

Supplementary information (CIF file)

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