Substrate-controlled Selectivity Switch in a Three-component Reaction: Sequential Synthesis of Spiro-oxazolidinedione-cyclopentenones and Hydroxy Enaminobarbiturates in Water

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 May 2

PMID 35492975

Authors

Mohammad Bagher Teimouri

Mahdi Heydari

Kazem Mohammadi

Affiliations

Soon will be listed here.

Abstract

An efficient eco-friendly catalyst-free three-component domino multicyclization for the synthesis of new spirobicyclic oxazolidinedione containing cyclopentenone moieties has been established by mixing amines, β-dicarbonyl compounds and ,'-dimethylalloxan in water at room temperature. This domino process involves multiple reactions such as enamination/aldol-like reaction/Stork enamine annulation/intramolecular cyclization under mild conditions.

References

Yu L, Qian R, Deng X, Wang F, Xu Q . Calcium-catalyzed reactions of element-H bonds. Sci Bull (Beijing). 2023; 63(15):1010-1016. DOI: 10.1016/j.scib.2018.06.002. View

Harada K, Kubo H, Tanaka A, Nishioka K . Identification of oxazolidinediones and thiazolidinediones as potent 17β-hydroxysteroid dehydrogenase type 3 inhibitors. Bioorg Med Chem Lett. 2011; 22(1):504-7. DOI: 10.1016/j.bmcl.2011.10.095. View

Cox J, Chu H, Yang C, Shen H, Wu Z, Balsells J . Mineralocorticoid receptor antagonists: identification of heterocyclic amide replacements in the oxazolidinedione series. Bioorg Med Chem Lett. 2014; 24(7):1681-4. DOI: 10.1016/j.bmcl.2014.02.057. View

Melhado A, Brenzovich Jr W, Lackner A, Toste F . Gold-catalyzed three-component coupling: oxidative oxyarylation of alkenes. J Am Chem Soc. 2010; 132(26):8885-7. PMC: 2904393. DOI: 10.1021/ja1034123. View

Adams G, Carroll P, Smith 3rd A . Access to the akuammiline family of alkaloids: total synthesis of (+)-scholarisine A. J Am Chem Soc. 2012; 135(1):519-28. PMC: 3557466. DOI: 10.1021/ja3111626. View

Grant T, West F . A new approach to the nazarov reaction via sequential electrocyclic ring opening and ring closure. J Am Chem Soc. 2006; 128(29):9348-9. DOI: 10.1021/ja063421a. View

Unruh G, Birney D . The stereochemistry of the thermal cheletropic decarbonylation of 3-cyclopentenone as determined by multiphoton infrared photolysis/thermolysis. J Am Chem Soc. 2003; 125(28):8529-33. DOI: 10.1021/ja0353661. View

Inagaki F, Kinebuchi M, Miyakoshi N, Mukai C . Formal synthesis of (+)-nakadomarin A. Org Lett. 2010; 12(8):1800-3. DOI: 10.1021/ol100412f. View

Yang C, Shen H, Wu Z, Chu H, Cox J, Balsells J . Discovery of novel oxazolidinedione derivatives as potent and selective mineralocorticoid receptor antagonists. Bioorg Med Chem Lett. 2013; 23(15):4388-92. DOI: 10.1016/j.bmcl.2013.05.077. View

10.

Trost B, Pinkerton A . A three-component coupling approach to cyclopentanoids. J Org Chem. 2001; 66(23):7714-22. DOI: 10.1021/jo010593b. View

11.

Namba K, Inai M, Sundermeier U, Greshock T, Williams R . Synthetic Studies on Palau'amine. Construction of the Cyclopentane Core via an Asymmetric 1,3-Dipolar Cycloaddition. Tetrahedron Lett. 2011; 51(50):6557-6559. PMC: 3030269. DOI: 10.1016/j.tetlet.2010.10.037. View

12.

Aggarwal V, Belfield A . Catalytic asymmetric Nazarov reactions promoted by chiral Lewis acid complexes. Org Lett. 2003; 5(26):5075-8. DOI: 10.1021/ol036133h. View

13.

Dow R, Bechle B, CHOU T, Clark D, Hulin B, Stevenson R . Benzyloxazolidine-2,4-diones as potent hypoglycemic agents. J Med Chem. 1991; 34(5):1538-44. DOI: 10.1021/jm00109a003. View

14.

Menjo Y, Hamajima A, Sasaki N, Hamada Y . Asymmetric aziridination of cyclic enones using chiral diamine catalysts and its application to the total synthesis of (-)-agelastatin A. Org Lett. 2011; 13(21):5744-7. DOI: 10.1021/ol2023054. View

15.

Simeonov S, Nunes J, Guerra K, Kurteva V, Afonso C . Synthesis of Chiral Cyclopentenones. Chem Rev. 2016; 116(10):5744-893. DOI: 10.1021/cr500504w. View

16.

He W, Sun X, Frontier A . Polarizing the Nazarov cyclization: efficient catalysis under mild conditions. J Am Chem Soc. 2003; 125(47):14278-9. DOI: 10.1021/ja037910b. View

17.

Tsukamoto S, Ichihara M, Wanibuchi F, Usuda S, Hidaka K, Harada M . Synthesis and structure-activity studies of a series of spirooxazolidine-2,4-diones: 4-oxa analogues of the muscarinic agonist 2-ethyl-8-methyl-2,8-diazaspiro[4.5]decane-1,3-dione. J Med Chem. 1993; 36(16):2292-9. DOI: 10.1021/jm00068a005. View

18.

Blanco-Urgoiti J, Anorbe L, Perez-Serrano L, Dominguez G, Perez-Castells J . The Pauson-Khand reaction, a powerful synthetic tool for the synthesis of complex molecules. Chem Soc Rev. 2004; 33(1):32-42. DOI: 10.1039/b300976a. View

19.

Moreira R, Santana A, Iley J, Neres J, Douglas K, Horton P . Design, synthesis, and enzymatic evaluation of N1-acyloxyalkyl- and N1-oxazolidin-2,4-dion-5-yl-substituted beta-lactams as novel inhibitors of human leukocyte elastase. J Med Chem. 2005; 48(15):4861-70. DOI: 10.1021/jm0501331. View

20.

Dickson D, Wardrop D . Total synthesis of (+/-)-agelastatin A, a potent inhibitor of osteopontin-mediated neoplastic transformations. Org Lett. 2009; 11(6):1341-4. PMC: 2671850. DOI: 10.1021/ol900133v. View