Cu-catalyzed arylation of the amino group in the indazole ring: regioselective synthesis of pyrazolo-carbazoles
| Autor: | Prakash Kannaboina, Devendra K. Dhaked, Parthasarathi Das, Ram A. Vishwakarma, K. Anil Kumar, Prasad V. Bharatam |
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| Rok vydání: | 2015 |
| Předmět: |
Models
Molecular Quantum chemical Indazole Indazoles Chemistry Carbazole Aryl Organic Chemistry Carbazoles Molecular Conformation Regioselectivity Stereoisomerism Chemistry Techniques Synthetic Ring (chemistry) Biochemistry Medicinal chemistry Catalysis Substrate Specificity chemistry.chemical_compound Pyrazoles Organic chemistry Physical and Theoretical Chemistry Copper |
| Zdroj: | Organic & Biomolecular Chemistry. 13:1481-1491 |
| ISSN: | 1477-0539 1477-0520 |
| DOI: | 10.1039/c4ob02044h |
| Popis: | Cu(II)-catalyzed cross-coupling of various aryl boronic acids with 5 and 6-amino indazoles has resulted in (arylamino)-indazoles. These (arylamino)-indazoles have been utilized in synthesizing medicinally important pyrazole-fused carbazoles via Pd(II)-catalyzed cross-dehydrogenative coupling (CDC). This combined N-arylation/C-H arylation strategy has been successfully applied to the regioselective synthesis of polyheterocycles 3,6-dihydropyrazolo[3,4-c]carbazoles and 1,6-dihydro pyrazolo[4,3-c]carbazoles. Quantum chemical analysis has been carried out to understand the regioselectivity and to trace the potential energy surface of the entire reaction upon 5-N-aryl-indazole conversion to the corresponding carbazole. |
| Databáze: | OpenAIRE |
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