Copper‐Catalyzed CNH2 Arylation of 2‐Aminobenzimidazoles and Related C‐Amino‐NH‐azoles. Issue 13 (7th June 2016)

• Record Type: Journal Article
• Authors: Rao, Desaboini Nageswar; Rasheed, Sk.; Kumar, Karampoori Anil; Reddy, Annem Siva; Das, Parthasarathi
• Is Part Of: Advanced synthesis & catalysis. Volume 358:Issue 13(2016)
• Page Start: 2126
• Page End: 2133
• Publication Date: 2016-06-07
• Subjects: aminoazoles -- Chan–Lam coupling -- copper catalysts -- open‐flask chemistry -- selective N‐arylation; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201600035
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A copper(II)‐catalyzed selective CNH2 arylation of 2‐aminobenzimidazoles and related C‐amino‐NH‐azoles was achieved in presence of 2, 2′‐bipyridine and cesium carbonate at 60 °C under open air conditions and this is first method for the copper‐catalyzed selective CNH2 arylation in the presence of other reactive nucleophilic sites. Previously unexplored heteroaromatics possessing multiple nucleophilic sites that are selectively arylated at the CNH2 position are obtained, providing an exceptional tool for rapid delivery of a diverse array of medicinally important CNH(aryl) derivatives of aminoazoles without any protection/deprotection of ring NH bonds. It is first example for the selective CNH2 arylation of 5‐aminoindazole, 4‐aminopyrazole, 5‐aminopyrazole, 9 H ‐purine‐6‐amine, and 1 H ‐pyrazolo[3, 4‐ d ]pyrimidin‐4‐amine derivatives. Abstract :