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通过三组分多米诺过程高效、非对映选择性合成新型吡唑基吡咯里嗪和吡唑基吡咯烷衍生物。

Highly efficient and diastereoselective synthesis of new pyrazolylpyrrolizine and pyrazolylpyrrolidine derivates by a three-component domino process.

作者信息

Quiroga Jairo, Gálvez Jaime, Abonia Rodrigo, Insuasty Braulio, Ortíz Alejandro, Cobo Justo, Nogueras Manuel

机构信息

Heterocyclic Compounds Research Group, Department of Chemistry, Universidad del Valle, Cali 760032, Colombia.

Department of Inorganic and Organic Chemistry, Universidad de Jaén, Jaén 23071, Spain.

出版信息

Molecules. 2014 Apr 4;19(4):4284-300. doi: 10.3390/molecules19044284.

DOI:10.3390/molecules19044284
PMID:24714191
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6270732/
Abstract

Diastereoselective reactions between 4-formylpyrazoles, N-substituted maleimides and glycine derivates led to new series of pyrazolyldipyrrolo [3,4-a:3',4'-f]pyrrolizines and pyrazolylpyrrolo[3,4-c]pyrroles in good yields. The reactions proceeded by a domino process through azomethine ylides formed in situ via a 1,3-dipolar cycloaddition reaction.

摘要

4-甲酰基吡唑、N-取代马来酰亚胺与甘氨酸衍生物之间的非对映选择性反应以良好的产率生成了一系列新型的吡唑基二吡咯并[3,4-a:3',4'-f]吡咯嗪和吡唑基吡咯并[3,4-c]吡咯。反应通过多米诺过程进行,该过程经由1,3-偶极环加成反应原位形成的甲亚胺叶立德。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb4b/6270732/c555ca98a422/molecules-19-04284-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb4b/6270732/231bc0467501/molecules-19-04284-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb4b/6270732/10598e1238c4/molecules-19-04284-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb4b/6270732/56c564c77278/molecules-19-04284-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb4b/6270732/70e642e363be/molecules-19-04284-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb4b/6270732/0bf314d42db2/molecules-19-04284-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb4b/6270732/b220ccdc8775/molecules-19-04284-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb4b/6270732/33fecab47e91/molecules-19-04284-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb4b/6270732/557e4fb6676c/molecules-19-04284-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb4b/6270732/c555ca98a422/molecules-19-04284-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb4b/6270732/231bc0467501/molecules-19-04284-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb4b/6270732/10598e1238c4/molecules-19-04284-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb4b/6270732/56c564c77278/molecules-19-04284-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb4b/6270732/70e642e363be/molecules-19-04284-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb4b/6270732/0bf314d42db2/molecules-19-04284-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb4b/6270732/b220ccdc8775/molecules-19-04284-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb4b/6270732/33fecab47e91/molecules-19-04284-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb4b/6270732/557e4fb6676c/molecules-19-04284-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb4b/6270732/c555ca98a422/molecules-19-04284-g004.jpg

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1
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Acta Crystallogr C. 2013 Aug;69(Pt 8):915-9. doi: 10.1107/S0108270113017563. Epub 2013 Jul 13.
2
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Acta Crystallogr C. 2012 Nov;68(Pt 11):o439-42. doi: 10.1107/S0108270112039856. Epub 2012 Oct 18.
3
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4
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5
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6
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9
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Angew Chem Int Ed Engl. 2011 Jul 4;50(28):6234-46. doi: 10.1002/anie.201006515. Epub 2011 Jun 27.
10
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J Org Chem. 2011 May 20;76(10):4210-2. doi: 10.1021/jo200601y. Epub 2011 Apr 20.