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Iodine/Water‐Mediated Oxidation of o ‐Alkynylaroyl Compounds and Application of the Products of Oxidation in the Synthesis of Nitrogen Heterocycles
Author(s) -
Sakthivel Karuppusamy,
Srinivasan Kannupal
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300046
Subject(s) - chemistry , quinoxaline , benzimidazole , iodine , organic chemistry , natural product , combinatorial chemistry , nitrogen
A facile iodine/water‐mediated oxidation of the triple bond of o ‐alkynylaroyl compounds to furnish tricarbonyl compounds is reported. The reaction proceeds through the formation of isochromenol intermediates by the assistance of the neighbouring aroyl group. The product tricarbonyl compounds are versatile synthetic precursors that, upon treatment with mono‐ and diamines, hydrazines and amino alcohols, afford various heterocyclic scaffolds such as isoindolinones, phthalazines, benzimidazoisoquinolinones, quinoxalines and benzimidazole‐quinoxaline hybrid compounds. Mechanistic aspects of the formation of the above heterocycles are discussed. Finally, a short synthetic route to the isoindolinone natural product, aristolactam BII is reported.