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Iron‐Catalyzed Annulation of 1,2‐Diamines and Diazodicarbonyls for Diverse and Polyfunctionalized Quinoxalines, Pyrazines, and Benzoquinoxalines in Water
Author(s) -
Pandit Rameshwar Prasad,
Kim Sung Hong,
Lee Yong Rok
Publication year - 2016
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.201600503
Subject(s) - annulation , chemistry , quinoxaline , catalysis , tandem , domino , combinatorial chemistry , cascade reaction , organic chemistry , reaction conditions , materials science , composite material
A novel and facile iron‐catalyzed tandem annulation of o ‐phenylenediamines and diazocarbonyls in water for the construction of polyfunctionalized quinoxalines has been developed. The key strategy includes the one‐pot domino N−H insertion, cyclization, and oxidation reactions. This protocol offers a safe and mild synthetic approach to access a variety of quinoxaline derivatives in high yields. This methodology also allows the formation of biologically interesting pyrazines and benzoquinoxalines.