Electron deficient alkynes reactivity against binucleophilic compounds

Identifier:  TFG:1710

Handle: https://hdl.handle.net/20.500.11797/TFG1710

Authors:  Morales Vidal, Jordi

Abstract:
Nowadays, bacteria have developed resistance against many antibiotics, for this reason, it is needed to look for new antibiotics. With the aim of finding products that could be converted in compounds with antibacterial activity, the reactivity of two electron deficient alkynes against binucleophilic species was tested and promising results were obtained. Theses two alkynes are (E)-dimethyl hex-2-en-4-ynedioate (DMHD) and dimethyl 2,4-hexadiyndioate (dialkyne). On the one hand, in reference to DMHD, its reactivity was tested against phenylhydrazine, methylhydrazine and hydrazine. In the first two cases the results were not good according to our objective. Anyway, the reactivity of DMHD against hydrazine seemed to be promising. Two interesting products with structures that suggest to be converted in compounds to be tested as new antibiotics were found. These products are a solid lactam (E-3-(1’H-2’,3’-dihydro-3’-oxopyrazol-5’-yl)prop-2- enoat) and an oily diester (methyl-2-(1’H-4’,5’-dihydro-3’-methoxycarbonyl-pyrazol-5’- yl) acetate). On the other hand, the reactivity of dialkyne against N,N’-dimethylthiourea was tested. In this case two interesting products were isolated too but in very little amounts. This low yield was caused due to the fact that dialkyne synthesis was not efficient. For this reason, the procedure to obtain the dialkyne needs to be improved. Despite this fact, it was proved that the chemistry of the dialkyne against binucleophilic species is possible. Hence, the next step could be test its reactivity against hydrazine which is thought that could generate interesting products to convert to compounds for testing new antibiotics.