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CuI 催化的 4-碘吡唑与醇的偶联反应：在 Withasomnine 和同系物合成中的应用。

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

机构信息

Department of Pharmaceutical Organic Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan.

出版信息

Molecules. 2021 Jun 2;26(11):3370. doi: 10.3390/molecules26113370.

DOI:10.3390/molecules26113370
PMID:34199652
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8199780/
Abstract

The direct 4-alkoxylation of 4-iodo-1-pyrazoles with alcohols was achieved by a CuI-catalyzed coupling protocol. The optimal reaction conditions employed excess alcohol and potassium -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.

摘要

碘化 1-吡唑与醇的直接 4-烷氧基化反应是通过 CuI 催化偶联实现的。优化的反应条件是在 130°C 下微波辐射 1 小时，使用过量的醇和叔丁醇钾（2 当量），CuI（20mol%）和 3,4,7,8-四甲基-1,10-菲咯啉（20mol%）作为催化剂。本方法有效地应用于合成瓦他索宁及其六元和七元环同系物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d8a1/8199780/a4497804623b/molecules-26-03370-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d8a1/8199780/ef21719cbf28/molecules-26-03370-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d8a1/8199780/a4dbfac8d590/molecules-26-03370-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d8a1/8199780/a235e1130cb3/molecules-26-03370-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d8a1/8199780/a4497804623b/molecules-26-03370-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d8a1/8199780/ef21719cbf28/molecules-26-03370-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d8a1/8199780/a4dbfac8d590/molecules-26-03370-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d8a1/8199780/a235e1130cb3/molecules-26-03370-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d8a1/8199780/a4497804623b/molecules-26-03370-sch003.jpg

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