A Passerini-type condensation for the synthesis of α-acyloxycarboxamides starting from simple and readily available inputs, including an isocyanide, aldehydes and water in the presence of trimethylsilyl azide as a catalyst under reflux conditions in toluene in good yields, is described.
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A passerini-type condensation: a carboxylic acid-free approach for the synthesis of the α-acyloxycarboxamides.
Comb Chem High Throughput Screen
December 2013
Faculty of Chemistry, Shahid Beheshti University, G. C., P. O. Box 19396-4716, Tehran, Iran.
A Passerini-type condensation for the synthesis of α-acyloxycarboxamides starting from simple and readily available inputs, including an isocyanide, aldehydes and water in the presence of trimethylsilyl azide as a catalyst under reflux conditions in toluene in good yields, is described.
View Article and Find Full Text PDFFacile procedure for generating side chain functionalized poly(alpha-hydroxy acid) copolymers from aldehydes via a versatile Passerini-type condensation.
Org Lett
August 2010
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, USA.
A general method for synthesizing alpha-hydroxy N-acylindoles in one-pot via an acid-catalyzed condensation of a convertible isonitrile with water and various aldehydes is presented. These intermediates were incorporated into poly(alpha-hydroxy acid) copolymers bearing residues with functionalizable side chains, which could be further modified through Cu(I)-catalyzed azide-alkyne cylcoaddition reactions. This versatile synthetic strategy provides access to side chain functionalized poly(alpha-hydroxy acid) copolymers from readily available aldehydes, making it potentially useful as an approach to synthesize biodegradable polymers with new, tunable properties.
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