title: Cu-catalyzed arylation of the amino group in the indazole ring: regioselective synthesis of pyrazolo-carbazoles.
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.
authors.affiliation: Academy of Scientific and Innovative Research(AcSIR), New Delhi, India.
authors.forename: K
authors.initials: K
authors.lastname: Anil Kumar
authors.forename: Prakash
authors.initials: P
authors.lastname: Kannaboina
authors.forename: Devendra K
authors.initials: DK
authors.lastname: Dhaked
authors.forename: Ram A
authors.initials: RA
authors.lastname: Vishwakarma
authors.forename: Prasad V
authors.initials: PV
authors.lastname: Bharatam
authors.forename: Parthasarathi
authors.initials: P
authors.lastname: Das
mesh_terms: D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D003300:Copper / Q000737:chemistry*; D007191:Indazoles / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D011720:Pyrazoles / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D002227:Carbazoles; D007191:Indazoles; D011720:Pyrazoles; C041514:carbazole; D003300:Copper