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通过达参反应简便合成官能化螺[吲哚啉-3,2'-氧杂环丁烷]-2-酮。

Facile synthesis of functionalized spiro[indoline-3,2'-oxiran]-2-ones by Darzens reaction.

机构信息

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

出版信息

Beilstein J Org Chem. 2013 May 13;9:918-24. doi: 10.3762/bjoc.9.105. Print 2013.

DOI:10.3762/bjoc.9.105
PMID:23766807
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3678858/
Abstract

A series of functionalized spiro[indoline-3,2'-oxiran]-2-ones was efficiently synthesized by Darzens reaction of phenacyl bromides with isatins both with N-alkyl groups and without N-substituent in the presence of potassium carbonate as a base catalyst. When two equivalents phenacyl bromides were used in the reaction, the N-substitution reaction of isatin also finished with the formation of spiro-oxirane-oxindoles.

摘要

通过在碳酸钾作为碱催化剂的存在下,用溴苯乙酮与具有 N-烷基和无 N-取代基的靛红进行 Darzens 反应,高效合成了一系列官能化的螺[吲哚啉-3,2'-恶嗪]-2-酮。当反应中使用两当量的溴苯乙酮时,靛红的 N-取代反应也完成,并形成了螺-氧杂环戊烷-氧吲哚。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc9e/3678858/606a20ac1511/Beilstein_J_Org_Chem-09-918-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc9e/3678858/8a53a581d2e5/Beilstein_J_Org_Chem-09-918-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc9e/3678858/b08a915b91f7/Beilstein_J_Org_Chem-09-918-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc9e/3678858/17411da91c7c/Beilstein_J_Org_Chem-09-918-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc9e/3678858/606a20ac1511/Beilstein_J_Org_Chem-09-918-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc9e/3678858/8a53a581d2e5/Beilstein_J_Org_Chem-09-918-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc9e/3678858/b08a915b91f7/Beilstein_J_Org_Chem-09-918-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc9e/3678858/17411da91c7c/Beilstein_J_Org_Chem-09-918-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc9e/3678858/606a20ac1511/Beilstein_J_Org_Chem-09-918-g004.jpg

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本文引用的文献

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Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione.通过芳胺、色酮和环戊烷-1,3-二酮的三组分反应合成螺[dihydropyridine-oxindoles]。
Beilstein J Org Chem. 2013;9:8-14. doi: 10.3762/bjoc.9.2. Epub 2013 Jan 3.
2
Facile synthesis of spiro[indoline-3,3'-pyrrolo[1,2-a]quinolines] and spiro[indoline-3,1'-pyrrolo[2,1-a]isoquinolines] via 1,3-dipolar cycloaddition reactions of heteroaromatic ammonium salts with 3-phenacylideneoxindoles.通过杂环铵盐与 3-苯甲酰亚甲基氧吲哚的 1,3-偶极环加成反应,简便合成螺[吲哚啉-3,3'-吡咯[1,2-a]喹啉]和螺[吲哚啉-3,1'-吡咯[2,1-a]异喹啉]。
Org Biomol Chem. 2012 Dec 21;10(47):9452-63. doi: 10.1039/c2ob26849c. Epub 2012 Nov 1.
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Facile synthesis of dispirooxindole-fused heterocycles via domino 1,4-dipolar addition and Diels-Alder reaction of in situ generated Huisgen 1,4-dipoles.通过原位生成的Huisgen 1,4-二偶极子的 1,4-偶极加成和 Diels-Alder 反应,简便合成了螺环氧化吲哚杂环。
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