Use of a convertible isocyanide for generation of Ugi reaction derivatives on solid support: Synthesis of α-acylaminoesters and pyrroles

Autor:	Ali M. Strocker, Robert W. Armstrong, Thomas A. Keating, Paul A. Tempest
Rok vydání:	1996
Předmět:	Four component Chemistry Isocyanide Organic Chemistry Condensation Succinic anhydride Alcohol Biochemistry chemistry.chemical_compound Acetylene Drug Discovery Ugi reaction Organic chemistry Linker
Zdroj:	Tetrahedron Letters. 37:1149-1152
ISSN:	0040-4039
DOI:	10.1016/0040-4039(96)00012-3
Popis:	The Ugi four component condensation employing 1-isocyanocyclohexene as a convertible isocyanide has been adapted to solid supported synthesis. Using Wang or Rink resin and a linker derived from succinic anhydride, Ugi reactions proceeded smoothly. The products were then converted under acidic alcohol conditions to esters, acids, and to pyrroles via 1,3-dipolar cycloadditions to an acetylene. The intermediate in both transformations is a 1,3-oxazolinium-5-one arising from cycloelimination of the cyclohexenamide from the Ugi product.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::00373c322385ccf22215d08b39dd6e55 https://doi.org/10.1016/0040-4039(96)00012-3 Zobrazit plný text záznamu Full Text from ScienceDirect