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串联 Cu 催化的烯酮亚胺形成和分子内亲核试剂捕获：从 1-(邻乙酰氨基苯基)丙炔醇合成 1,2-二氢-2-亚氨基喹啉。

Tandem Cu-catalyzed ketenimine formation and intramolecular nucleophile capture: Synthesis of 1,2-dihydro-2-iminoquinolines from 1-(o-acetamidophenyl)propargyl alcohols.

机构信息

Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram extension, Sitapur Road, P.O. Box 173, Lucknow 226031, India.

Academy of Scientific and Innovative Research, New Delhi 110001, India.

出版信息

Beilstein J Org Chem. 2014 May 28;10:1255-1260. doi: 10.3762/bjoc.10.125. eCollection 2014.

DOI:10.3762/bjoc.10.125
PMID:24991276
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4077525/
Abstract

The copper-catalyzed ketenimine formation reaction of 1-(o-acetamidophenyl)propargyl alcohols with various sulfonyl azides is found to undergo a concomitant intramolecular nucleophile attack to generate 1,2-dihydro-2-iminoquinolines after aromatization (via elimination of acetyl and hydroxy groups) and tautomerization. The reaction produces 4-substituted and 3,4-unsubstituted title compounds in moderate to good yields under mild reaction conditions.

摘要

发现 1-(邻乙酰氨基苯基)丙炔醇与各种磺酰基叠氮化物的铜催化酮亚胺形成反应在芳构化（通过乙酰基和羟基的消除）和互变异构后经历同时的分子内亲核进攻，生成 1,2-二氢-2-亚氨基喹啉。在温和的反应条件下，该反应以中等至良好的收率生成 4-取代和 3,4-未取代的标题化合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a3b0/4077525/35f905c54c43/Beilstein_J_Org_Chem-10-1255-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a3b0/4077525/ff2145348ce9/Beilstein_J_Org_Chem-10-1255-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a3b0/4077525/ea9b5c16db09/Beilstein_J_Org_Chem-10-1255-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a3b0/4077525/196909b875d3/Beilstein_J_Org_Chem-10-1255-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a3b0/4077525/35f905c54c43/Beilstein_J_Org_Chem-10-1255-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a3b0/4077525/ff2145348ce9/Beilstein_J_Org_Chem-10-1255-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a3b0/4077525/ea9b5c16db09/Beilstein_J_Org_Chem-10-1255-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a3b0/4077525/196909b875d3/Beilstein_J_Org_Chem-10-1255-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a3b0/4077525/35f905c54c43/Beilstein_J_Org_Chem-10-1255-g002.jpg

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本文引用的文献

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Angew Chem Int Ed Engl. 1998 Sep 18;37(17):2371-2373. doi: 10.1002/(SICI)1521-3773(19980918)37:17<2371::AID-ANIE2371>3.0.CO;2-N.
2
Cu-catalyzed conversion of propargyl acetates to E-α,β-unsaturated amides via ketenimine formation with sulfonyl azides.铜催化的炔丙基乙酸酯通过与磺酰叠氮形成烯酮亚胺转化为E-α,β-不饱和酰胺。
J Org Chem. 2014 Jan 17;79(2):823-8. doi: 10.1021/jo402570t. Epub 2013 Dec 27.
3
A 1,3-amino group migration route to form acrylamidines.
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Chem Commun (Camb). 2014 Jan 11;50(3):323-5. doi: 10.1039/c3cc47182a. Epub 2013 Nov 14.
4
Cu-catalyzed 1,2-dihydroisoquinolines synthesis from o-ethynyl benzacetals and sulfonyl azides.铜催化邻炔基苯乙缩醛与磺酰叠氮的 1,2-二氢异喹啉合成。
Org Lett. 2013 Nov 15;15(22):5894-7. doi: 10.1021/ol402996x. Epub 2013 Nov 5.
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J Org Chem. 2013 Sep 6;78(17):8816-20. doi: 10.1021/jo401094j. Epub 2013 Aug 13.
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J Org Chem. 2013 Jun 21;78(12):5878-88. doi: 10.1021/jo400499r. Epub 2013 Jun 3.
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Parallel copper catalysis: diastereoselective synthesis of polyfunctionalized azetidin-2-imines.平行铜催化：多官能化氮杂环丁烷-2-亚胺的非对映选择性合成。
Org Lett. 2013 Jun 7;15(11):2668-71. doi: 10.1021/ol4010323. Epub 2013 May 13.