Unknown

Dataset Information

0

Regioselective alkylation of a versatile indazole: Electrophile scope and mechanistic insights from density functional theory calculations.

ABSTRACT: Herein, we report a pair of regioselective N 1- and N 2 -alkylations of a versatile indazole, methyl 5-bromo-1H-indazole-3-carboxylate (6) and the use of density functional theory (DFT) to evaluate their mechanisms. Over thirty N 1- and N 2-alkylated products were isolated in over 90% yield regardless of the conditions. DFT calculations suggest a chelation mechanism produces the N 1-substituted products when cesium is present and other non-covalent interactions (NCIs) drive the N 2-product formation. Methyl 1H-indazole-7-carboxylate (18) and 1H-indazole-3-carbonitrile (21) were also subjected to the reaction conditions and their mechanisms were evaluated. The N 1- and N 2-partial charges and Fukui indices were calculated for compounds 6, 18, and 21 via natural bond orbital (NBO) analyses which further support the suggested reaction pathways.

SUBMITTER: Lu P 

PROVIDER: S-EPMC11318628 | biostudies-literature | 2024

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Regioselective alkylation of a versatile indazole: Electrophile scope and mechanistic insights from density functional theory calculations.

Lu Pengcheng P   Juarez Luis L   Wiget Paul A PA   Zhang Weihe W   Raman Krishnan K   Kotian Pravin L PL  

Beilstein journal of organic chemistry 20240809

Herein, we report a pair of regioselective <i>N</i> <sup>1</sup>- and <i>N</i> <sup>2</sup> <i>-</i>alkylations of a versatile indazole, methyl 5-bromo-1<i>H</i>-indazole-3-carboxylate (<b>6</b>) and the use of density functional theory (DFT) to evaluate their mechanisms. Over thirty <i>N</i> <sup>1</sup>- and <i>N</i> <sup>2</sup>-alkylated products were isolated in over 90% yield regardless of the conditions. DFT calculations suggest a chelation mechanism produces the <i>N</i> <sup>1</sup>-sub  ...[more]

Similar Datasets

Unknown Copper-catalyzed stereo- and regioselective hydrophosphorylation of terminal alkynes: scope and mechanistic study.
| S-EPMC9241361 | biostudies-literature
Unknown Antioxidant Properties of Kynurenines: Density Functional Theory Calculations.
| S-EPMC5115656 | biostudies-literature
Unknown Mechanistic Features in Al(I)-Mediated Oxidative Addition of Aryl C-F Bonds: Insights From Density Functional Theory Calculations.
| S-EPMC6733912 | biostudies-literature
Unknown Double-Hybrid Density Functional Theory for Core Excitations: Theory and Benchmark Calculations.
| S-EPMC9979613 | biostudies-literature
Unknown Challenging Density Functional Theory Calculations with Hemes and Porphyrins.
| S-EPMC4848975 | biostudies-literature
Unknown Regioselective Alkylation of Pyridinium Riboses.
| S-EPMC7250371 | biostudies-literature
Unknown Density functional theory calculations on Mossbauer parameters of nonheme iron nitrosyls.
| S-EPMC2777692 | biostudies-literature
Unknown Regioselective <i>N</i>-alkylation of the 1<i>H</i>-indazole scaffold; ring substituent and <i>N</i>-alkylating reagent effects on regioisomeric distribution.
| S-EPMC8353588 | biostudies-literature
Unknown Mechanistic investigations on Pinnick oxidation: a density functional theory study.
| S-EPMC7062072 | biostudies-literature
Unknown Three-Component Cross-Electrophile Coupling: Regioselective Electrochemical Dialkylation of Alkenes.
| S-EPMC10625357 | biostudies-literature