| Autor: |
Pengcheng Lu, Luis Juarez, Paul A. Wiget, Weihe Zhang, Krishnan Raman, Pravin L. Kotian |
| Jazyk: |
angličtina |
| Rok vydání: |
2024 |
| Předmět: |
|
| Zdroj: |
Beilstein Journal of Organic Chemistry, Vol 20, Iss 1, Pp 1940-1954 (2024) |
| Druh dokumentu: |
article |
| ISSN: |
1860-5397 |
| DOI: |
10.3762/bjoc.20.170 |
| Popis: |
Herein, we report a pair of regioselective N1- and N2-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 N1- and N2-alkylated products were isolated in over 90% yield regardless of the conditions. DFT calculations suggest a chelation mechanism produces the N1-substituted products when cesium is present and other non-covalent interactions (NCIs) drive the N2-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 N1- and N2-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. |
| Databáze: |
Directory of Open Access Journals |
| Externí odkaz: |
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