New conditions for the synthesis of thiophenes via the Knoevenagel/Gewald reaction sequence. Application to the synthesis of a multitargeted kinase inhibitor

Autor:	Maureen A. McLaughlin, Joan Dalla Riva Toma, Jianzhang Mei, Thomas Hameury, Jason S. Tedrow, Anthony R. Haight, David M. Barnes
Rok vydání:	2006
Předmět:	Acetic acid chemistry.chemical_compound chemistry Kinase Organic Chemistry Drug Discovery Total synthesis Sequence (biology) Knoevenagel condensation Gewald reaction Biochemistry Combinatorial chemistry Catalysis
Zdroj:	Tetrahedron. 62:11311-11319
ISSN:	0040-4020
DOI:	10.1016/j.tet.2006.07.008
Popis:	Novel conditions have been developed for the preparation of substituted 2-aminothiophenes employing the Knoevenagel condensation followed by the Gewald reaction. The benefits of these conditions are their mildness, and the ease of product isolation. Thus, the Knoevenagel condensation is run in the presence of hexamethyldisilazane and acetic acid, which combine to perform the roles of desiccant, and catalyst. The Gewald reaction is performed with inorganic base in THF/water, which suppresses byproduct formation. This process has been employed in the total synthesis of a multitargeted kinase inhibitor.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::422a96ef4c126567293b97cc94f16cb1 https://doi.org/10.1016/j.tet.2006.07.008 Zobrazit plný text záznamu Full Text from ScienceDirect