Cu-catalyzed arylation of the amino group in the indazole ring: regioselective synthesis of pyrazolo-carbazoles

Anil Kumar, K. ; Kannaboina, Prakash ; Dhaked, Devendra K. ; Vishwakarma, Ram A. ; Bharatam, Prasad V. ; Das, Parthasarathi (2015) Cu-catalyzed arylation of the amino group in the indazole ring: regioselective synthesis of pyrazolo-carbazoles Organic & Biomolecular Chemistry, 13 (5). pp. 1481-1491. ISSN 1477-0520

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Official URL: http://doi.org/10.1039/C4OB02044H

Related URL: http://dx.doi.org/10.1039/C4OB02044H

Abstract

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.

Item Type:Article
Source:Copyright of this article belongs to Royal Society of Chemistry.
ID Code:116425
Deposited On:12 Apr 2021 09:36
Last Modified:12 Apr 2021 09:36

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