Theoretical Analysis of the Regioselective Electrophilic Chloration and Chemioselective Esterification of the pyrazolo[1,5-a]pyridine-2,3-dicarboxylic acid

2020/09/16 by S. Jorio, M. El Idrissi
#3-dicarboxylic acid. #5-a]pyridine-2 #DFT calculation #Sulfonyl chlorides #chemoselectivity #pyrazolo[1 #regioselectivity

paper · doi:10.48317/imist.prsm/morjchem-v8i1.17120

Abstract

The reaction between the pyrazolo[1,5-a]pyridine-2,3-dicarboxylic acid 1 and SOCl2 has been studied within the Density Functional Theory (DFT) B3LYP/6-31G(d,p) computational level. Examination of the conceptual DFT reactivity indices permit the elucidation of the reactivity, and the regio- and chemoselectivity experimentally observed. The possible regioselective channels and chemoselective channels were explored and characterized. Analysis of the energies associated with the different reaction pathways shows that this reaction is completely chemioselective and regioselective, in conformity with the experimental results.

Related

• Study of regioselectivity in the synthesis of substituted 1,2,3-triazole via [3+2] cycloaddition, using density functional theory (DFT) with in-silico evaluation
• The mechanism, the chemoselectivity and the regioselectivity of the 1-Benzyl-4-ethynyl-1H-[1,2,3]triazole and 1-Azidomethyl-4-tert-butyl-benzene in [3+2] cycloaddition reactions: a DFT study
• A DFT study of the mechanism and regioselectivity of the reaction between diethyl trichloro-methyl phosphonate and diphenyl methyl phosphinite
• Theoretical study of the regio- and stereoselectivity of the 1,3-DC reaction of 2,3,4,5-tetrahydropyridine-l-oxide with methyl crotonate
• Theoretical study of the formation of α-bromoglycidic esters in aliphatic series using the DFT quantum mechanical method with B3LYP/6-311G (d, p)