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串联四组分反应高效合成含取代氨基酸乙酯的二氢噻吩

Tandem four-component reaction for efficient synthesis of dihydrothiophene with substituted amino acid ethyl esters.

作者信息

Sun Jing, Zhang Yu, Yan Chao-Guo

机构信息

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

出版信息

RSC Adv. 2018 Jun 20;8(40):22498-22505. doi: 10.1039/c8ra03605e. eCollection 2018 Jun 19.

DOI:10.1039/c8ra03605e
PMID:35539758
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9081350/
Abstract

The one-pot four-component reaction of aromatic aldehydes, malononitrile, 1,3-thiazolidinedione and ethyl glycinate hydrochloride in ethanol in the presence of triethylamine afforded -dihydrothiophene ureidoformamide derivatives in moderate to good yields. The other α-amino acid ethyl esters resulted in the corresponding diastereoisomeric dihydrothiophene derivatives with various molecular ratios. The functionalized thiophene derivatives were also successfully prepared by sequential dehydrogenation reaction with DDQ.

摘要

在三乙胺存在下，芳香醛、丙二腈、1,3 - 噻唑烷二酮和甘氨酸乙酯盐酸盐在乙醇中进行一锅四组分反应，以中等至良好的产率得到了二氢噻吩脲甲酰胺衍生物。其他α - 氨基酸乙酯则生成了具有不同分子比例的相应非对映异构二氢噻吩衍生物。通过与2,3 - 二氯 - 5,6 - 二氰基 - 1,4 - 苯醌（DDQ）进行连续脱氢反应，也成功制备了功能化噻吩衍生物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bbee/9081350/c8888b220590/c8ra03605e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bbee/9081350/bf5fdb7f438a/c8ra03605e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bbee/9081350/bef30e4ab4c1/c8ra03605e-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bbee/9081350/c018ad06146e/c8ra03605e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bbee/9081350/2bf5009a0648/c8ra03605e-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bbee/9081350/c8888b220590/c8ra03605e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bbee/9081350/bf5fdb7f438a/c8ra03605e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bbee/9081350/bef30e4ab4c1/c8ra03605e-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bbee/9081350/c018ad06146e/c8ra03605e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bbee/9081350/2bf5009a0648/c8ra03605e-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bbee/9081350/c8888b220590/c8ra03605e-s2.jpg

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Angew Chem Int Ed Engl. 2017 Apr 10;56(16):4579-4582. doi: 10.1002/anie.201701409. Epub 2017 Mar 23.
2
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Org Lett. 2016 Oct 21;18(20):5408-5411. doi: 10.1021/acs.orglett.6b02805. Epub 2016 Oct 10.
3
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J Org Chem. 2016 Nov 4;81(21):10532-10537. doi: 10.1021/acs.joc.6b01315. Epub 2016 Sep 29.
4
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6
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7
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8
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Tetrahedron. 2011 Feb 4;67(5):1002-1010. doi: 10.1016/j.tet.2010.11.104.