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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]。

Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione.

机构信息

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

出版信息

Beilstein J Org Chem. 2013;9:8-14. doi: 10.3762/bjoc.9.2. Epub 2013 Jan 3.

DOI:10.3762/bjoc.9.2
PMID:23399791
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3566796/
Abstract

A fast and convenient protocol for the synthesis of novel spiro[dihydropyridine-oxindole] derivatives in satisfactory yields was developed by the three-component reactions of arylamine, isatin and cyclopentane-1,3-dione in acetic acid at room temperature. On the other hand the condensation of isatin with two equivalents of cyclopentane-1,3-dione gave 3,3-bis(2-hydroxy-5-oxo-cyclopent-1-enyl)oxindole in high yields. The reaction mechanism and substrate scope of this novel reaction is briefly discussed.

摘要

一种快速便捷的方法，可在醋酸中室温条件下，通过芳胺、色胺和环戊烷-1,3-二酮的三组分反应，以满意的收率合成新型螺[二氢吡啶-氧吲哚]衍生物。另一方面，色胺与两当量的环戊烷-1,3-二酮缩合得到 3,3-双（2-羟基-5-氧代环戊-1-烯基）氧吲哚，产率很高。简要讨论了这种新反应的反应机制和底物范围。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6a8/3566796/42f598fa851c/Beilstein_J_Org_Chem-09-08-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6a8/3566796/d1e2b170fc7f/Beilstein_J_Org_Chem-09-08-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6a8/3566796/cdca0f19cc09/Beilstein_J_Org_Chem-09-08-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6a8/3566796/f4f24d4bce33/Beilstein_J_Org_Chem-09-08-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6a8/3566796/6f5c5c37f4e9/Beilstein_J_Org_Chem-09-08-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6a8/3566796/780bacf4776e/Beilstein_J_Org_Chem-09-08-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6a8/3566796/eba7bae961ce/Beilstein_J_Org_Chem-09-08-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6a8/3566796/42f598fa851c/Beilstein_J_Org_Chem-09-08-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6a8/3566796/d1e2b170fc7f/Beilstein_J_Org_Chem-09-08-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6a8/3566796/cdca0f19cc09/Beilstein_J_Org_Chem-09-08-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6a8/3566796/f4f24d4bce33/Beilstein_J_Org_Chem-09-08-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6a8/3566796/6f5c5c37f4e9/Beilstein_J_Org_Chem-09-08-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6a8/3566796/780bacf4776e/Beilstein_J_Org_Chem-09-08-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6a8/3566796/eba7bae961ce/Beilstein_J_Org_Chem-09-08-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6a8/3566796/42f598fa851c/Beilstein_J_Org_Chem-09-08-g008.jpg

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Highly efficient hydrogen-bonding catalysis of the Diels-Alder reaction of 3-vinylindoles and methyleneindolinones provides carbazolespirooxindole skeletons.高氢键催化 3-乙烯基吲哚与亚甲基色满酮的 Diels-Alder 反应，生成咔唑螺吲哚酮骨架。
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