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N-芳基-3-氧代丁酰胺中芳基取代基对其与 5-氨基-3-甲基异唑和水杨醛的多组分反应行为的意外影响。

The unexpected influence of aryl substituents in N-aryl-3-oxobutanamides on the behavior of their multicomponent reactions with 5-amino-3-methylisoxazole and salicylaldehyde.

机构信息

Division of Chemistry of Functional Materials, SSI "Institute for Single Crystals" NAS of Ukraine, Lenin Ave. 60, Kharkiv 61001, Ukraine ; Faculty of Chemistry, V. N. Karazin Kharkiv National University, Svobody sq. 4, Kharkiv 61022, Ukraine.

Division of Chemistry of Functional Materials, SSI "Institute for Single Crystals" NAS of Ukraine, Lenin Ave. 60, Kharkiv 61001, Ukraine.

出版信息

Beilstein J Org Chem. 2014 Dec 17;10:3019-30. doi: 10.3762/bjoc.10.320. eCollection 2014.

DOI:10.3762/bjoc.10.320
PMID:25670972
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4311697/
Abstract

The switchable three-component reactions of 5-amino-3-methylisoxazole, salicylaldehyde and N-aryl-3-oxobutanamides under different conditions were studied and discussed. The unexpected influence of the aryl substituent in N-aryl-3-oxobutanamides on the behavior of the reaction was discovered. The key influence of ultrasonication and Lewis acid catalysts led to an established protocol to selectively obtain two or three types of heterocyclic scaffolds depending on the substituent in the N-aryl moiety.

摘要

研究并讨论了在不同条件下，5-氨基-3-甲基异恶唑、水杨醛和 N-芳基-3-氧代丁酰胺的可切换三组分反应。发现 N-芳基-3-氧代丁酰胺中芳基取代基对反应行为的意外影响。超声和路易斯酸催化剂的关键影响导致建立了一种方案，根据 N-芳基部分的取代基，选择性地获得两种或三种类型的杂环支架。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7159/4311697/80ae3f4fa437/Beilstein_J_Org_Chem-10-3019-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7159/4311697/ddc948d773e7/Beilstein_J_Org_Chem-10-3019-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7159/4311697/de4ab48ee4f7/Beilstein_J_Org_Chem-10-3019-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7159/4311697/538d7020ef85/Beilstein_J_Org_Chem-10-3019-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7159/4311697/2802d95eeccb/Beilstein_J_Org_Chem-10-3019-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7159/4311697/956e3902ebe8/Beilstein_J_Org_Chem-10-3019-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7159/4311697/92bfb4cd0b33/Beilstein_J_Org_Chem-10-3019-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7159/4311697/4050fd9dec75/Beilstein_J_Org_Chem-10-3019-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7159/4311697/49fe059e0ad9/Beilstein_J_Org_Chem-10-3019-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7159/4311697/80ae3f4fa437/Beilstein_J_Org_Chem-10-3019-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7159/4311697/ddc948d773e7/Beilstein_J_Org_Chem-10-3019-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7159/4311697/de4ab48ee4f7/Beilstein_J_Org_Chem-10-3019-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7159/4311697/538d7020ef85/Beilstein_J_Org_Chem-10-3019-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7159/4311697/2802d95eeccb/Beilstein_J_Org_Chem-10-3019-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7159/4311697/956e3902ebe8/Beilstein_J_Org_Chem-10-3019-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7159/4311697/92bfb4cd0b33/Beilstein_J_Org_Chem-10-3019-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7159/4311697/4050fd9dec75/Beilstein_J_Org_Chem-10-3019-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7159/4311697/49fe059e0ad9/Beilstein_J_Org_Chem-10-3019-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7159/4311697/80ae3f4fa437/Beilstein_J_Org_Chem-10-3019-g006.jpg

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