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Carboxylic Acid Free Novel Isocyanide‐Based Reactions
Author(s) -
Soeta Takahiro,
Ukaji Yutaka
Publication year - 2014
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.201300021
Subject(s) - isocyanide , chemistry , intramolecular force , ugi reaction , combinatorial chemistry , electrophile , nucleophile , carboxylic acid , cycloaddition , organic chemistry , catalysis
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 α‐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.