Journal
CHEMICAL RECORD
Volume 14, Issue 1, Pages 101-116Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/tcr.201300021
Keywords
cycloaddition; isocyanides; multicomponent reactions; Passerini reaction; Ugi reaction
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Funding
- Japan Society for the Promotion of Science [20850017, 24750037, 24350022]
- Grants-in-Aid for Scientific Research [20850017, 24750037, 25620028] Funding Source: KAKEN
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In order to develop a practical method for the construction of drug-like and heterocyclic compounds, we have designed a novel Passerini- or Ugi-type reaction system where a compound (which we write in the general form as Z-X) composed of an electrophilic (Z) and a nucleophilic group (X) could essentially perform the same function as the carboxylic acid. Based on this concept, we have developed the O-silylative Passerini reaction and the borinic acid catalyzed -addition of isocyanides to aldehydes and water. In addition, we have designed and demonstrated the addition reaction of isocyanides to nitrones in the presence of TMSCl to afford the corresponding 1,2,3,4-tetrahydroisoquinoline-1-carboxyamides. Furthermore, a novel [5+1] cycloaddition of isocyanide was explored with C,N-cyclic N-acyl azomethine imines as a 1,5-dipole via a strategy involving intramolecular trapping of the isocyanide.
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