CuI-Catalyzed Coupling Reactions of 4-Iodopyrazoles and Alcohols: Application toward Withasomnine and Homologs

The direct 4-alkoxylation of 4-iodo-1H-pyrazoles with alcohols was achieved by a CuI-catalyzed coupling protocol. The optimal reaction conditions employed excess alcohol and potassium t-butoxide (2 equiv) in the presence of CuI (20 mol%) and 3,4,7,8-tetramethyl-1,10-phenanthroline (20 mol%) at 130 °...

Descripción completa

Detalles Bibliográficos
Autores principales: Usami, Yoshihide, Kubo, Yumika, Takagaki, Toshiki, Kuroiwa, Nao, Ono, Jun, Nishikawa, Kohei, Nakamizu, Ayaka, Tatsui, Yuya, Harusawa, Shinya, Hayama, Noboru, Yoneyama, Hiroki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8199780/
https://www.ncbi.nlm.nih.gov/pubmed/34199652
http://dx.doi.org/10.3390/molecules26113370
Descripción
Sumario:The direct 4-alkoxylation of 4-iodo-1H-pyrazoles with alcohols was achieved by a CuI-catalyzed coupling protocol. The optimal reaction conditions employed excess alcohol and potassium t-butoxide (2 equiv) in the presence of CuI (20 mol%) and 3,4,7,8-tetramethyl-1,10-phenanthroline (20 mol%) at 130 °C for 1 h under microwave irradiation. The present method was efficiently applied to the synthesis of withasomnine and its six- and seven-membered cyclic homologs.

Ejemplares similares