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铜催化多组分反应高效合成多种螺四氢咔唑

Copper-catalyzed multicomponent reactions for the efficient synthesis of diverse spirotetrahydrocarbazoles.

作者信息

Zhan Shao-Cong, Fang Ren-Jie, Sun Jing, Yan Chao-Guo

机构信息

College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China.

出版信息

Beilstein J Org Chem. 2022 Jul 7;18:796-808. doi: 10.3762/bjoc.18.80. eCollection 2022.

DOI:10.3762/bjoc.18.80
PMID:35875709
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9273986/
Abstract

In the presence of copper sulfate, three- or four-component reactions of 2-methylindole, aromatic aldehydes and various cyclic dienophiles in refluxing toluene afforded diverse spirotetrahydrocarbazoles. This reaction is an important development of the Levy reaction by using 2-methylindole to replace ethyl indole-2-acetate and successfully provides facile access to important polysubstituted spiro[carbazole-3,3'-indolines], spiro[carbazole-2,3'-indolines], spiro[carbazole-3,5'-pyrimidines] and spiro[carbazole-3,1'-cycloalkanes] in satisfactory yields and with high diastereoselectivity.

摘要

在硫酸铜存在下，2-甲基吲哚、芳香醛和各种环状亲双烯体在回流甲苯中进行的三组分或四组分反应可得到多种螺四氢咔唑。该反应是对利维反应的重要发展，通过使用2-甲基吲哚取代吲哚-2-乙酸乙酯，成功地以令人满意的产率和高非对映选择性便捷地合成了重要的多取代螺[咔唑-3,3'-二氢吲哚]、螺[咔唑-2,3'-二氢吲哚]、螺[咔唑-3,5'-嘧啶]和螺[咔唑-3,1'-环烷烃]。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd88/9273986/c04398233a66/Beilstein_J_Org_Chem-18-796-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd88/9273986/10dfc9c9167a/Beilstein_J_Org_Chem-18-796-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd88/9273986/dab4ec833084/Beilstein_J_Org_Chem-18-796-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd88/9273986/7e4a852ec734/Beilstein_J_Org_Chem-18-796-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd88/9273986/4220229a1451/Beilstein_J_Org_Chem-18-796-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd88/9273986/357b7e546143/Beilstein_J_Org_Chem-18-796-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd88/9273986/ea182f68afa3/Beilstein_J_Org_Chem-18-796-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd88/9273986/c04398233a66/Beilstein_J_Org_Chem-18-796-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd88/9273986/10dfc9c9167a/Beilstein_J_Org_Chem-18-796-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd88/9273986/dab4ec833084/Beilstein_J_Org_Chem-18-796-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd88/9273986/7e4a852ec734/Beilstein_J_Org_Chem-18-796-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd88/9273986/4220229a1451/Beilstein_J_Org_Chem-18-796-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd88/9273986/357b7e546143/Beilstein_J_Org_Chem-18-796-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd88/9273986/ea182f68afa3/Beilstein_J_Org_Chem-18-796-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd88/9273986/c04398233a66/Beilstein_J_Org_Chem-18-796-g008.jpg

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