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.
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。
相似文献
1
Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione.
Beilstein J Org Chem. 2013;9:8-14. doi: 10.3762/bjoc.9.2. Epub 2013 Jan 3.
2
DNA Fragmentation, Cell Cycle Arrest, and Docking Study of Novel Bis Spiro-cyclic 2-oxindole of Pyrimido[4,5-b]quinoline-4,6-dione Derivatives Against Breast Carcinoma.
Curr Cancer Drug Targets. 2018;18(4):372-381. doi: 10.2174/1568009617666170630143311.
3
Multicomponent Synthesis of Spiro-dihydropyridine Oxindoles Cascade Spiro-cyclization of Knoevenagel/Aza-Michael Adducts.
J Org Chem. 2022 Nov 4;87(21):13556-13563. doi: 10.1021/acs.joc.2c01063. Epub 2022 Oct 4.
4
Convenient synthesis of triphenylphosphanylidene spiro[cyclopentane-1,3'-indolines] and spiro[cyclopent[3]ene-1,3'-indolines] via three-component reactions. [Corrected].
Org Lett. 2014 May 16;16(10):2654-7. doi: 10.1021/ol5008394. Epub 2014 Apr 18.
5
Lambert Salt-Initiated Development of Friedel-Crafts Reaction on Isatin to Access Distinct Derivatives of Oxindoles.
J Org Chem. 2021 Dec 17;86(24):17833-17847. doi: 10.1021/acs.joc.1c02058. Epub 2021 Dec 7.
6
Catalytic enantioselective amide allylation of isatins and its application in the synthesis of 2-oxindole derivatives spiro-fused to the α-methylene-γ-butyrolactone functionality.
Chemistry. 2014 Aug 25;20(35):11091-100. doi: 10.1002/chem.201403357. Epub 2014 Jul 22.
7
Isatin and its derivatives: a survey of recent syntheses, reactions, and applications.
Medchemcomm. 2019 Jan 15;10(3):351-368. doi: 10.1039/c8md00585k. eCollection 2019 Mar 1.
8
Selective Synthesis of Diverse Spiro-oxindole-fluorene Derivatives via a DABCO-Promoted Annulation Reaction of Bindone and 3-Methyleneoxindoles.
J Org Chem. 2021 Nov 5;86(21):14705-14719. doi: 10.1021/acs.joc.1c01513. Epub 2021 Oct 18.
9
Synthesis of functionalized spiro[indoline-3,4'-pyridines] and spiro[indoline-3,4'-pyridinones] via one-pot four-component reactions.
Beilstein J Org Chem. 2013 May 2;9:846-51. doi: 10.3762/bjoc.9.97. Print 2013.
10
Domino Reactions Enable Zn-Mediated Direct Synthesis of Spiro-Fused 2-Oxindole-α-Methylene-γ-Butyrolactones/Lactams from Isatin Derivatives and 2-(Bromomethyl)acrylates.
Molecules. 2024 Jul 30;29(15):3612. doi: 10.3390/molecules29153612.
引用本文的文献
1
High-performance modified LDH for green one-pot synthesis of pyrido[2,3-]pyrimidines.
Heliyon. 2024 Dec 12;11(1):e41149. doi: 10.1016/j.heliyon.2024.e41149. eCollection 2025 Jan 15.
2
Three-component reaction of o-aminophenol (o-phenylenediamine), dialkyl acetylenedicarboxylate and 3-phenacylideneoxindolines.
Mol Divers. 2019 Feb;23(1):123-135. doi: 10.1007/s11030-018-9853-0. Epub 2018 Jul 30.
3
Methyl isocyanide as a convertible functional group for the synthesis of spirocyclic oxindole γ-lactams via post-Ugi-4CR/transamidation/cyclization in a one-pot, three-step sequence.
Beilstein J Org Chem. 2018 Apr 18;14:875-883. doi: 10.3762/bjoc.14.74. eCollection 2018.
4
Regioselectivity and diastereoselectivity of three-component reaction of α-amino acid, dialkyl acetylenedicarboxylates and 2-arylidene-1,3-indanediones.
Sci Rep. 2017 Sep 29;7(1):12418. doi: 10.1038/s41598-017-12361-z.
5
One-pot four-component reaction for convenient synthesis of functionalized 1-benzamidospiro[indoline-3,4'-pyridines].
Beilstein J Org Chem. 2014 Nov 14;10:2671-6. doi: 10.3762/bjoc.10.281. eCollection 2014.
6
Facile synthesis of functionalized spiro[indoline-3,2'-oxiran]-2-ones by Darzens reaction.
Beilstein J Org Chem. 2013 May 13;9:918-24. doi: 10.3762/bjoc.9.105. Print 2013.
本文引用的文献
1
Highly efficient hydrogen-bonding catalysis of the Diels-Alder reaction of 3-vinylindoles and methyleneindolinones provides carbazolespirooxindole skeletons.
J Am Chem Soc. 2011 Aug 17;133(32):12354-7. doi: 10.1021/ja203812h. Epub 2011 Jul 22.
2
Highly regio- and diastereoselective construction of spirocyclopenteneoxindoles through phosphine-catalyzed [3 + 2] annulation of Morita-Baylis-Hillman carbonates with isatylidene malononitriles.
Org Lett. 2011 Jul 1;13(13):3348-51. doi: 10.1021/ol201094f. Epub 2011 Jun 8.
3
Base catalyzed multicomponent synthesis of spiroheterocycles with fused heterosystems.
Mol Divers. 2011 Aug;15(3):781-9. doi: 10.1007/s11030-011-9309-2. Epub 2011 Mar 20.
4
Simple three-component method for the synthesis of spiroindeno[1,2-b]pyrido[2,3-d]pyrimidine-5,3'-indolines.
ACS Comb Sci. 2011 Jan 10;13(1):96-9. doi: 10.1021/co1000053. Epub 2010 Nov 9.
5
Sonochemical multi-component synthesis of spirooxindoles.
Ultrason Sonochem. 2011 Sep;18(5):1153-9. doi: 10.1016/j.ultsonch.2010.12.004. Epub 2010 Dec 21.
6
Titanium-catalyzed stereoselective synthesis of spirooxindole oxazolines.
Org Lett. 2011 Feb 4;13(3):418-21. doi: 10.1021/ol1027305. Epub 2010 Dec 27.
7
Ultrasound-assisted synthesis of 2,2'-(2-oxoindoline-3,3-diyl)bis(1H-indene-1,3(2H)-dione) derivatives.
Ultrason Sonochem. 2011 Jan;18(1):415-8. doi: 10.1016/j.ultsonch.2010.07.010. Epub 2010 Jul 27.
8
Regioselective synthesis of novel spiropyrrolidines and spirothiapyrrolizidines through multicomponent 1,3-dipolar cycloaddition reaction of azomethine ylides.
J Comb Chem. 2010 Sep 13;12(5):633-7. doi: 10.1021/cc100035q.
9
Pyridine core activation via 1,5-electrocyclization of vinyl pyridinium ylides generated from bromo isomerized Morita-Baylis-Hillman adduct of isatin and pyridine: synthesis of 3-spirodihydroindolizine oxindoles.
Org Lett. 2010 May 7;12(9):2108-11. doi: 10.1021/ol100591r.
10
Ultrasound-assisted three-component synthesis of 3-(5-amino-1H-pyrazol-4-yl)-3-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)indolin-2-ones in water.
Ultrason Sonochem. 2010 Mar;17(3):587-91. doi: 10.1016/j.ultsonch.2009.11.017. Epub 2009 Nov 27.
Zotero 插件