Carboxylic acid free novel isocyanide-based reactions.
Chem Rec
; 14(1): 101-16, 2014 Feb.
Article
en En
| MEDLINE
| ID: mdl-24449481
ABSTRACT
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.
Palabras clave
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Ácidos Carboxílicos
/
Cianuros
Idioma:
En
Revista:
Chem Rec
Asunto de la revista:
QUIMICA
Año:
2014
Tipo del documento:
Article
País de afiliación:
Japón