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通过丙烯酰胺和芳基丙烯酸与色酮和α-氨基酸的三组分反应，区域选择性合成螺氧吲哚吡咯烷和吡咯里西啶。

The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids.

机构信息

State Scientific Institution "Institute for Single Crystals" of National Academy of Sciences of Ukraine, 60, Lenin ave., Kharkov, 61178, Ukraine.

State Scientific Institution "Institute for Single Crystals" of National Academy of Sciences of Ukraine, 60, Lenin ave., Kharkov, 61178, Ukraine ; Antidiabetic Drug Laboratory, State Institution "V.J. Danilevsky Institute of Problems of Endocrine Pathology at the Academy of Medical Sciences of Ukraine", 10, Artem St., Kharkov, 61002, Ukraine.

出版信息

Beilstein J Org Chem. 2014 Jan 9;10:117-26. doi: 10.3762/bjoc.10.8.

DOI:10.3762/bjoc.10.8
PMID:24454564
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3896290/
Abstract

The regioselective three-component condensation of azomethine ylides derived from isatins and α-amino acids with acrylamides or aroylacrylic acids as dipolarophiles has been realized through a one-pot 1,3-dipolar cycloaddition protocol. Decarboxylation of 2'-aroyl-2-oxo-1,1',2,2',5',6',7',7a'-octahydrospiro[indole-3,3'-pyrrolizine]-1'-carboxylic acids is accompanied by cyclative rearrangement with formation of dihydropyrrolizinyl indolones.

摘要

通过一锅 1,3-偶极环加成反应，实现了靛红亚胺叶立德与α-氨基酸、丙烯酰胺或芳基丙烯酸的区域选择性三组分缩合反应。2'-芳基-2-氧代-1,1',2,2',5',6',7',7a'-八氢螺[吲哚-3,3'-吡咯嗪]-1'-羧酸发生脱羧反应，同时伴随着环化重排，生成二氢吡咯并[吲哚]酮。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcf1/3896290/fac20b4d374b/Beilstein_J_Org_Chem-10-117-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcf1/3896290/ee147a983af1/Beilstein_J_Org_Chem-10-117-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcf1/3896290/28d0c73e6819/Beilstein_J_Org_Chem-10-117-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcf1/3896290/044773c90f41/Beilstein_J_Org_Chem-10-117-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcf1/3896290/1b8aeef2bec2/Beilstein_J_Org_Chem-10-117-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcf1/3896290/28c4b4589b01/Beilstein_J_Org_Chem-10-117-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcf1/3896290/ec5a9a122490/Beilstein_J_Org_Chem-10-117-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcf1/3896290/b4bc03989321/Beilstein_J_Org_Chem-10-117-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcf1/3896290/58f4f75d3fa6/Beilstein_J_Org_Chem-10-117-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcf1/3896290/d406c61a375d/Beilstein_J_Org_Chem-10-117-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcf1/3896290/fac20b4d374b/Beilstein_J_Org_Chem-10-117-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcf1/3896290/ee147a983af1/Beilstein_J_Org_Chem-10-117-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcf1/3896290/28d0c73e6819/Beilstein_J_Org_Chem-10-117-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcf1/3896290/044773c90f41/Beilstein_J_Org_Chem-10-117-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcf1/3896290/1b8aeef2bec2/Beilstein_J_Org_Chem-10-117-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcf1/3896290/28c4b4589b01/Beilstein_J_Org_Chem-10-117-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcf1/3896290/ec5a9a122490/Beilstein_J_Org_Chem-10-117-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcf1/3896290/b4bc03989321/Beilstein_J_Org_Chem-10-117-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcf1/3896290/58f4f75d3fa6/Beilstein_J_Org_Chem-10-117-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcf1/3896290/d406c61a375d/Beilstein_J_Org_Chem-10-117-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcf1/3896290/fac20b4d374b/Beilstein_J_Org_Chem-10-117-g011.jpg

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Bioorg Med Chem Lett. 2013 May 15;23(10):2979-83. doi: 10.1016/j.bmcl.2013.03.027. Epub 2013 Mar 23.
2
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3
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4
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