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Bis(dibenzylideneacetone)palladium(0)/ tert‐ Butyl Nitrite‐ Catalyzed Cyclization of o ‐Alkynylanilines with tert‐ Butyl Nitrite: Synthesis and Applications of Indazole 2‐Oxides
Author(s) -
Senadi Gopal Chandru,
Wang JiQi,
Gore Babasaheb Sopan,
Wang JehJeng
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700456
Subject(s) - chemistry , indazole , catalysis , nitrite , palladium , combinatorial chemistry , substrate (aquarium) , medicinal chemistry , organic chemistry , oceanography , nitrate , geology
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 involves the formation of three new bonds via N ‐nitrosation (N–NO), 5‐ exo ‐dig cyclization (C–N) and oxidation (C=O). The notable features are the mild reaction conditions, broad substrate scope and dual role of TBN as an 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).