Carboxylic acid free novel isocyanide-based reactions.
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.
Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa, 920-1192, Japan. soeta@se.kanazawa-u.ac.jp.
Takahiro
T
Soeta
Yutaka
Y
Ukaji
D000447:Aldehydes / Q000737:chemistry; D001889:Borinic Acids / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D003486:Cyanides / Q000737:chemistry*; D061565:Cycloaddition Reaction; D006571:Heterocyclic Compounds / Q000737:chemistry; D012821:Silanes / Q000737:chemistry; D014867:Water / Q000737:chemistry
D000447:Aldehydes; D001889:Borinic Acids; D002264:Carboxylic Acids; D003486:Cyanides; D006571:Heterocyclic Compounds; D012821:Silanes; D014867:Water
Passerini reaction; Ugi reaction; cycloaddition; isocyanides; multicomponent reactions