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芳香胺、1,3 - 二羰基化合物与α - 溴乙醛缩二乙醇的三组分反应，用于合成-(杂)芳基 - 4,5 - 未取代的吡咯。

Three-component reactions of aromatic amines, 1,3-dicarbonyl compounds, and α-bromoacetaldehyde acetal to access -(hetero)aryl-4,5-unsubstituted pyrroles.

作者信息

Huang Wenbo, Wang Kaimei, Liu Ping, Li Minghao, Ke Shaoyong, Gu Yanlong

机构信息

National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, 8 Nanhu Avenue, Hongshan District, Wuhan 430064, China.

School of Chemistry and Chemical Engineering, The Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Shihezi City 832004, China.

出版信息

Beilstein J Org Chem. 2020 Nov 30;16:2920-2928. doi: 10.3762/bjoc.16.241. eCollection 2020.

DOI:10.3762/bjoc.16.241
PMID:33335599
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7722624/
Abstract

-(Hetero)aryl-4,5-unsubstituted pyrroles were synthesized from (hetero)arylamines, 1,3-dicarbonyl compounds, and α-bromoacetaldehyde acetal by using aluminum(III) chloride as a Lewis acid catalyst through [1 + 2 + 2] annulation. This new versatile methodology provides a wide scope for the synthesis of different functional -(hetero)aryl-4,5-unsubstituted pyrrole scaffolds, which can be further derived to access multisubstituted pyrrole-3-carboxamides. In the presence of 1.2 equiv of KI, a polysubstituted pyrazolo[3,4-]pyridine derivative was also successfully synthesized.

摘要

通过用三氯化铝作为路易斯酸催化剂，经由[1 + 2 + 2]环化反应，由（杂）芳胺、1,3 - 二羰基化合物和α - 溴乙醛缩二乙醇合成了（杂）芳基 - 4,5 - 未取代的吡咯。这种新的通用方法为合成不同官能团的（杂）芳基 - 4,5 - 未取代的吡咯骨架提供了广泛的适用范围，这些骨架可进一步衍生以得到多取代的吡咯 - 3 - 甲酰胺。在1.2当量的碘化钾存在下，还成功合成了一种多取代的吡唑并[3,4 - ]吡啶衍生物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/17be/7722624/1cbace13d498/Beilstein_J_Org_Chem-16-2920-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/17be/7722624/a37a88f5feff/Beilstein_J_Org_Chem-16-2920-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/17be/7722624/291c33c7988d/Beilstein_J_Org_Chem-16-2920-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/17be/7722624/1cbace13d498/Beilstein_J_Org_Chem-16-2920-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/17be/7722624/a37a88f5feff/Beilstein_J_Org_Chem-16-2920-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/17be/7722624/291c33c7988d/Beilstein_J_Org_Chem-16-2920-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/17be/7722624/1cbace13d498/Beilstein_J_Org_Chem-16-2920-g006.jpg

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