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通过氮丙啶环扩张 2-[(氮丙啶-1-基)-1-烷基/芳基/杂芳基亚甲基]丙二酸二乙酯合成新型 5-烷基/芳基/杂芳基取代的二乙基 3,4-二氢-2H-吡咯-4,4-二羧酸酯。

Synthesis of novel 5-alkyl/aryl/heteroaryl substituted diethyl 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates by aziridine ring expansion of 2-[(aziridin-1-yl)-1-alkyl/aryl/heteroaryl-methylene]malonic acid diethyl esters.

机构信息

Technology Development Centre, Custom Pharmaceutical Services, Dr. Reddy's Laboratories Ltd., Miyapur, Hyderabad -500 049, India.

出版信息

Beilstein J Org Chem. 2011;7:831-8. doi: 10.3762/bjoc.7.95. Epub 2011 Jun 20.

DOI:10.3762/bjoc.7.95
PMID:21804879
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3135249/
Abstract

A novel synthetic methodology has been developed for the synthesis of diethyl 5-alkyl/aryl/heteroaryl substituted 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates (also called 2-substituted pyrroline-4,5-dihydro-3,3-dicarboxylic acid diethyl esters) by iodide ion induced ring expansion of 2-[(aziridin-1-yl)-1-alkyl/aryl/heteroaryl-methylene]malonic acid diethyl esters in very good to excellent yields under mild reaction conditions. The electronic and steric impact of the substituents on the kinetics of ring expansion of N-vinyl aziridines to pyrrolines has been studied. Various diversely substituted novel pyrroline derivatives have been synthesized by this methodology and the products can be used as key intermediates in the synthesis of substituted pyrrolines, pyrroles and pyrrolidines.

摘要

一种新型的合成方法已经被开发出来，用于通过碘离子诱导 2-[(氮丙啶-1-基)-1-烷基/芳基/杂芳基亚甲基]丙二酸二乙酯的环扩张，来合成二乙基 5-烷基/芳基/杂芳基取代的 3,4-二氢-2H-吡咯-4,4-二羧酸酯（也称为 2-取代吡咯啉-4,5-二氢-3,3-二羧酸二乙酯），该方法在温和的反应条件下可以得到非常好的至优秀的产率。研究了取代基对 N-乙烯基氮丙啶环扩张为吡咯啉的动力学的电子和空间影响。通过这种方法合成了各种不同取代的新型吡咯啉衍生物，这些产物可以用作取代吡咯啉、吡咯和吡咯烷合成的关键中间体。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79c0/3135249/6e2521379c24/Beilstein_J_Org_Chem-07-831-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79c0/3135249/cafb6fda381e/Beilstein_J_Org_Chem-07-831-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79c0/3135249/22a21c6ccefc/Beilstein_J_Org_Chem-07-831-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79c0/3135249/7959a7e58922/Beilstein_J_Org_Chem-07-831-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79c0/3135249/c82bfe3b50d9/Beilstein_J_Org_Chem-07-831-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79c0/3135249/21d132d19b41/Beilstein_J_Org_Chem-07-831-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79c0/3135249/244320b4b9fc/Beilstein_J_Org_Chem-07-831-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79c0/3135249/eaa46377b6b6/Beilstein_J_Org_Chem-07-831-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79c0/3135249/6e2521379c24/Beilstein_J_Org_Chem-07-831-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79c0/3135249/cafb6fda381e/Beilstein_J_Org_Chem-07-831-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79c0/3135249/22a21c6ccefc/Beilstein_J_Org_Chem-07-831-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79c0/3135249/7959a7e58922/Beilstein_J_Org_Chem-07-831-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79c0/3135249/c82bfe3b50d9/Beilstein_J_Org_Chem-07-831-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79c0/3135249/21d132d19b41/Beilstein_J_Org_Chem-07-831-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79c0/3135249/244320b4b9fc/Beilstein_J_Org_Chem-07-831-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79c0/3135249/eaa46377b6b6/Beilstein_J_Org_Chem-07-831-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/79c0/3135249/6e2521379c24/Beilstein_J_Org_Chem-07-831-g009.jpg

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本文引用的文献

1
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Chem Commun (Camb). 2010 Jan 14;46(2):267-9. doi: 10.1039/b920564k. Epub 2009 Nov 27.
2
Nickel-catalyzed borylative ring opening of vinyl epoxides and aziridines.镍催化的乙烯基环氧化物和氮丙啶的硼化开环反应。
Org Lett. 2009 Aug 20;11(16):3762-5. doi: 10.1021/ol901429g.
3
Coupling of Vinyl Aziridines and Isocyanates.乙烯基氮丙啶与异氰酸酯的偶联反应
Tetrahedron Lett. 2008;49(27):4306-4309. doi: 10.1016/j.tetlet.2008.04.121.
4
Rearrangement of N-aryl-2-vinylaziridines to benzoazepines and dihydropyrroles: a synthetic and theoretical study.N-芳基-2-乙烯基氮杂环丙烷重排为苯并氮杂䓬和二氢吡咯：一项合成与理论研究。
Chemistry. 2009;15(5):1241-51. doi: 10.1002/chem.200801148.
5
Lewis acid catalyzed [1,3]-sigmatropic rearrangement of vinyl aziridines.路易斯酸催化的乙烯基氮杂环丙烷的[1,3]-σ迁移重排反应。
Org Lett. 2008 Nov 6;10(21):5023-6. doi: 10.1021/ol802123e. Epub 2008 Oct 9.
6
Synthesis of antiproliferative Cephalotaxus esters and their evaluation against several human hematopoietic and solid tumor cell lines: uncovering differential susceptibilities to multidrug resistance.抗增殖三尖杉酯类化合物的合成及其对几种人类造血和实体瘤细胞系的评估：揭示对多药耐药性的差异敏感性
Chemistry. 2008;14(14):4293-306. doi: 10.1002/chem.200701998.
7
Dynamic kinetic asymmetric allylic amination and acyl migration of vinyl aziridines with imido carboxylates.乙烯基氮杂环丙烷与酰亚胺羧酸盐的动态动力学不对称烯丙基胺化及酰基迁移反应
Angew Chem Int Ed Engl. 2007;46(32):6123-5. doi: 10.1002/anie.200700835.
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J Org Chem. 2005 Nov 11;70(23):9399-406. doi: 10.1021/jo051495j.