Pd(dba)2/tert-Butyl Nitrite (TBN) Catalyzed o-Alkynylanilines Cyclization to form Indazole 2-oxides

• Main Authors: Ji-Qi Wang, 王顗淇
• Other Authors: Jeh-Jeng Wang
• Format: Others
• Language: zh-TW
• Published: 2017
• Online Access: http://ndltd.ncl.edu.tw/handle/73378718149889743190

碩士 === 高雄醫學大學 === 醫藥暨應用化學系碩士在職專班 === 105 === An efficient method for the synthesis of 1-benzyl/arylindazole 2-oxides via a bis(dibenzylideneacetone)palladium(0) (Pd(dba)2)/tert-butyl nitrite (TBN)-catalyzed reaction of o-alkynylaniline derivatives with TBN is reported. The overall transformation involved the formation of three new bonds via N-nitrosation (N-NO), 5-exo-dig cyclization (C-N) and oxidation (C=O). The notable features were the mild reaction conditions, broad substrate scope and dual role of TBN as a NO source and redox co-catalyst. This strategy was implemented for the synthesis of indazole-3-carbaldehyde derivatives and the formal syntheses of pharmaceutically active YC-1, an anticancer agent (lonidamine), and the male contraceptive experimental drugs AF-2785 and adjudin (AF-2364).