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 °...

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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
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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
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author Usami, Yoshihide
Kubo, Yumika
Takagaki, Toshiki
Kuroiwa, Nao
Ono, Jun
Nishikawa, Kohei
Nakamizu, Ayaka
Tatsui, Yuya
Harusawa, Shinya
Hayama, Noboru
Yoneyama, Hiroki
author_facet Usami, Yoshihide
Kubo, Yumika
Takagaki, Toshiki
Kuroiwa, Nao
Ono, Jun
Nishikawa, Kohei
Nakamizu, Ayaka
Tatsui, Yuya
Harusawa, Shinya
Hayama, Noboru
Yoneyama, Hiroki
author_sort Usami, Yoshihide
collection PubMed
description 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.
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spelling pubmed-81997802021-06-14 CuI-Catalyzed Coupling Reactions of 4-Iodopyrazoles and Alcohols: Application toward Withasomnine and Homologs Usami, Yoshihide Kubo, Yumika Takagaki, Toshiki Kuroiwa, Nao Ono, Jun Nishikawa, Kohei Nakamizu, Ayaka Tatsui, Yuya Harusawa, Shinya Hayama, Noboru Yoneyama, Hiroki Molecules Article 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. MDPI 2021-06-02 /pmc/articles/PMC8199780/ /pubmed/34199652 http://dx.doi.org/10.3390/molecules26113370 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Usami, Yoshihide
Kubo, Yumika
Takagaki, Toshiki
Kuroiwa, Nao
Ono, Jun
Nishikawa, Kohei
Nakamizu, Ayaka
Tatsui, Yuya
Harusawa, Shinya
Hayama, Noboru
Yoneyama, Hiroki
CuI-Catalyzed Coupling Reactions of 4-Iodopyrazoles and Alcohols: Application toward Withasomnine and Homologs
title CuI-Catalyzed Coupling Reactions of 4-Iodopyrazoles and Alcohols: Application toward Withasomnine and Homologs
title_full CuI-Catalyzed Coupling Reactions of 4-Iodopyrazoles and Alcohols: Application toward Withasomnine and Homologs
title_fullStr CuI-Catalyzed Coupling Reactions of 4-Iodopyrazoles and Alcohols: Application toward Withasomnine and Homologs
title_full_unstemmed CuI-Catalyzed Coupling Reactions of 4-Iodopyrazoles and Alcohols: Application toward Withasomnine and Homologs
title_short CuI-Catalyzed Coupling Reactions of 4-Iodopyrazoles and Alcohols: Application toward Withasomnine and Homologs
title_sort cui-catalyzed coupling reactions of 4-iodopyrazoles and alcohols: application toward withasomnine and homologs
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8199780/
https://www.ncbi.nlm.nih.gov/pubmed/34199652
http://dx.doi.org/10.3390/molecules26113370
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