Regioselective synthesis of novel spiropyrrolidines and spirothiapyrrolizidines through multicomponent 1,3-dipolar cycloaddition reaction of azomethine ylides
- PMID: 20608736
- DOI: 10.1021/cc100035q
Regioselective synthesis of novel spiropyrrolidines and spirothiapyrrolizidines through multicomponent 1,3-dipolar cycloaddition reaction of azomethine ylides
Abstract
A series of novel spiropyrrolidines and spirothiapyrrolizidines were synthesized via a three-component 1,3-dipolar cycloaddition reaction of isatin or acenaphthenequinone, sarcosine or thiaproline and 4-hydroxy-6-methyl-3-((E)-3-phenylacryloyl)-2H-pyran-2-ones in refluxing ethanol. Advantages of this method include the availability of starting materials, mild reaction conditions, high yields, and the complete regioselectivity observed.
Similar articles
-
Ultrasound-promoted synthesis of novel spirooxindolo/spiroacenaphthen dicyano pyrrolidines and pyrrolizidines through regioselective azomethine ylide cycloaddition reaction.Ultrason Sonochem. 2011 Jan;18(1):49-53. doi: 10.1016/j.ultsonch.2010.05.016. Epub 2010 Jun 30. Ultrason Sonochem. 2011. PMID: 20692198
-
Catalytic asymmetric 1,3-dipolar cycloaddition of N-unprotected 2-oxoindolin-3-ylidene derivatives and azomethine ylides for the construction of spirooxindole-pyrrolidines.Org Biomol Chem. 2011 Mar 21;9(6):1980-6. doi: 10.1039/c0ob00943a. Epub 2011 Jan 26. Org Biomol Chem. 2011. PMID: 21270976
-
Synthesis of novel functionalized 3-spiropyrrolizidine and 3-spiropyrrolidine oxindoles from Baylis-Hillman adducts of isatin and heteroaldehydes with azomethine ylides via [3+2]-cycloaddition.Org Lett. 2007 Oct 11;9(21):4095-8. doi: 10.1021/ol701533d. Epub 2007 Sep 18. Org Lett. 2007. PMID: 17877359
-
1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives.Molecules. 2016 Jul 23;21(8):935. doi: 10.3390/molecules21080935. Molecules. 2016. PMID: 27455230 Free PMC article. Review.
-
Asymmetric 1,3-dipolar cycloadditons of stabilized azomethine ylides with nitroalkenes.Curr Top Med Chem. 2014;14(10):1271-82. doi: 10.2174/1568026614666140423112145. Curr Top Med Chem. 2014. PMID: 24758430 Review.
Cited by
-
An efficient synthesis of novel dispirooxindole derivatives via one-pot three-component 1,3-dipolar cycloaddition reactions.Molecules. 2012 Oct 26;17(11):12704-17. doi: 10.3390/molecules171112704. Molecules. 2012. PMID: 23103534 Free PMC article.
-
Molecular diversity of spirooxindoles. Synthesis and biological activity.Mol Divers. 2016 Feb;20(1):299-344. doi: 10.1007/s11030-015-9629-8. Epub 2015 Sep 29. Mol Divers. 2016. PMID: 26419598 Review.
-
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. Beilstein J Org Chem. 2013. PMID: 23399791 Free PMC article.
-
A facile synthesis of functionalized dispirooxindole derivatives via a three-component 1,3-dipolar cycloaddition reaction.Molecules. 2013 May 3;18(5):5142-54. doi: 10.3390/molecules18055142. Molecules. 2013. PMID: 23644979 Free PMC article.
-
Benzodioxole grafted spirooxindole pyrrolidinyl derivatives: synthesis, characterization, molecular docking and anti-diabetic activity.RSC Adv. 2022 Aug 25;12(37):24192-24207. doi: 10.1039/d2ra04452h. eCollection 2022 Aug 22. RSC Adv. 2022. PMID: 36128541 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources