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用于构建二氢异喹啉-1(2H)-酮和异喹啉-1,3(2H,4H)-二酮的取代N-烯丙基苯甲酰胺的级联烷基化反应

Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones.

作者信息

Qian Ping, Du Bingnan, Jiao Wei, Mei Haibo, Han Jianlin, Pan Yi

机构信息

School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, 210093, China.

School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, 210093, China; Institute for Chemistry & BioMedical Sciences, Nanjing University, Nanjing, 210093, China.

出版信息

Beilstein J Org Chem. 2016 Feb 17;12:301-8. doi: 10.3762/bjoc.12.32. eCollection 2016.

DOI:10.3762/bjoc.12.32
PMID:26977189
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4778529/
Abstract

An oxidative reaction for the synthesis of 4-alkyl-substituted dihydroisoquinolin-1(2H)-ones with N-allylbenzamide derivatives as starting materials has been developed. The radical alkylarylation reaction proceeds through a sequence of alkylation and intramolecular cyclization. The substituent on the C-C double bond was found to play a key role for the progress of the reaction to give the expected products with good chemical yields. Additionally, N-methacryloylbenzamides were also suitable substrates for the current reaction and provided the alkyl-substituted isoquinoline-1,3(2H,4H)-diones in good yield.

摘要

已经开发了一种以N-烯丙基苯甲酰胺衍生物为起始原料合成4-烷基取代二氢异喹啉-1(2H)-酮的氧化反应。自由基烷基芳基化反应通过烷基化和分子内环化序列进行。发现碳-碳双键上的取代基对反应的进行起着关键作用,能够以良好的化学产率得到预期产物。此外,N-甲基丙烯酰基苯甲酰胺也是当前反应的合适底物,并能以良好的产率提供烷基取代的异喹啉-1,3(2H,4H)-二酮。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2f5b/4778529/2a6a6f38dcac/Beilstein_J_Org_Chem-12-301-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2f5b/4778529/e9b89cfd3eff/Beilstein_J_Org_Chem-12-301-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2f5b/4778529/afbb9c167179/Beilstein_J_Org_Chem-12-301-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2f5b/4778529/c4559d982aca/Beilstein_J_Org_Chem-12-301-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2f5b/4778529/014915bbbf24/Beilstein_J_Org_Chem-12-301-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2f5b/4778529/0f9adca00ea1/Beilstein_J_Org_Chem-12-301-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2f5b/4778529/2a6a6f38dcac/Beilstein_J_Org_Chem-12-301-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2f5b/4778529/e9b89cfd3eff/Beilstein_J_Org_Chem-12-301-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2f5b/4778529/afbb9c167179/Beilstein_J_Org_Chem-12-301-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2f5b/4778529/c4559d982aca/Beilstein_J_Org_Chem-12-301-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2f5b/4778529/014915bbbf24/Beilstein_J_Org_Chem-12-301-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2f5b/4778529/0f9adca00ea1/Beilstein_J_Org_Chem-12-301-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2f5b/4778529/2a6a6f38dcac/Beilstein_J_Org_Chem-12-301-g007.jpg

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本文引用的文献

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Org Lett. 2015 Nov 20;17(22):5524-7. doi: 10.1021/acs.orglett.5b02356. Epub 2015 Oct 30.
2
Hydroxyalkylation-initiated radical cyclization of N-allylbenzamide for direct construction of isoquinolinone.
Org Lett. 2015 Jun 5;17(11):2724-7. doi: 10.1021/acs.orglett.5b01140. Epub 2015 May 26.
3
Rhenium-catalyzed dehydrogenative olefination of C(sp(3))-H bonds with hypervalent iodine(III) reagents.
Org Biomol Chem. 2015 Jun 7;13(21):5880-4. doi: 10.1039/c5ob00619h.
4
Oxidant-free rhodium(I)-catalyzed difunctionalization of acrylamide: an efficient approach to synthesize oxindoles.
Org Lett. 2015 May 1;17(9):2142-5. doi: 10.1021/acs.orglett.5b00732. Epub 2015 Apr 16.
5
Cascade couplings of N-alkyl-N-methacryloyl benzamides with ethers and benzenesulfonohydrazides to generate isoquinoline-1,3(2H,4H)-dione derivatives.N-烷基-N-甲基丙烯酰基苯甲酰胺与醚和苯磺酰肼的级联偶联反应以生成异喹啉-1,3(2H,4H)-二酮衍生物。
J Org Chem. 2015 Apr 17;80(8):4176-83. doi: 10.1021/acs.joc.5b00158. Epub 2015 Mar 26.
6
Metal-free oxidative functionalization of a C(sp(3))-H bond adjacent to nitrogen and intramolecular aromatic cyclization for the preparation of 6-amidophenanthridines.用于制备6-氨基菲啶的、与氮相邻的C(sp(3))-H键的无金属氧化官能团化及分子内芳香环化反应
J Org Chem. 2015 Mar 20;80(6):3151-8. doi: 10.1021/acs.joc.5b00058. Epub 2015 Mar 11.
7
Direct trifluoromethylthiolation of unactivated C(sp(3))-H using silver(I) trifluoromethanethiolate and potassium persulfate.使用三氟甲烷硫代银和过硫酸钾直接对未活化的 C(sp(3))-H 进行三氟甲基化。
Angew Chem Int Ed Engl. 2015 Mar 23;54(13):4070-4. doi: 10.1002/anie.201411953. Epub 2015 Feb 23.
8
Metal-free oxidative functionalization of C(sp(3))-H bond adjacent to oxygen and radical addition to olefins.无金属促进的 C(sp(3))-H 键与氧相邻的氧化官能化反应和自由基对烯烃的加成反应。
Org Lett. 2015 Mar 6;17(5):1160-3. doi: 10.1021/acs.orglett.5b00088. Epub 2015 Feb 18.
9
Cobalt-catalyzed cross-dehydrogenative coupling reaction in water by visible light.钴催化的可见光促进的水中交叉脱氢偶联反应。
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10
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Adv Synth Catal. 2014 Aug 10;356(11-12):2719-2724. doi: 10.1002/adsc.201400032.