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Petasis Three-Component Coupling Reactions of Hydrazides for the Synthesis of Oxadiazolones and Oxazolidinones
Author(s) -
Sebastian T. Le Quement,
Thomas Flagstad,
Remi J. T. Mikkelsen,
Mette R. Hansen,
Michael Givskov,
Thomas E. Nielsen
Publication year - 2012
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/ol203280b
Subject(s) - chemistry , triphosgene , component (thermodynamics) , combinatorial chemistry , scope (computer science) , substrate (aquarium) , coupling reaction , ring (chemistry) , coupling (piping) , reaction conditions , organic chemistry , catalysis , computer science , programming language , mechanical engineering , physics , oceanography , geology , engineering , thermodynamics , phosgene
An application of readily available hydrazides in the Petasis 3-component coupling reaction is presented. An investigation of the substrate scope was performed to establish a general, synthetically useful protocol for the formation of hydrazido alcohols, which were selectively converted to oxazolidinone and oxadiazolone ring systems through triphosgene-mediated cyclization reactions.

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