Microwave-assisted Efficient and Facile Synthesis of Tetramic Acid Derivatives Via a One-pot Post-Ugi Cascade Reaction

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2020 Apr 23

PMID 32318123

Authors

Yong Li

Zheng Huang

Jia Xu

Yong Ding

Dian-Yong Tang

Jie Lei

Hong-Yu Li

Zhong-Zhu Chen

Zhi-Gang Xu

Affiliations

Soon will be listed here.

Abstract

A facile microwave-assisted method for the synthesis of tetramic acid derivatives has been developed through an Ugi/Dieckmann cyclization strategy with DBU. This two-step one-pot procedure afforded the targeted tetramic acid analogues in good yields. With commercially available Ugi starting materials, microwave irradiation, a simple operation, excellent yields, and a broad scope, this reaction has the potential to produce a large number of tetramic acid analogues, which cannot be easily accessed by the classic synthetic methods.

References

Singh B, Bisht S, Tripathi R . An efficient synthesis of tetramic acid derivatives with extended conjugation from L-ascorbic acid. Beilstein J Org Chem. 2006; 2:24. PMC: 1783862. DOI: 10.1186/1860-5397-2-24. View

Fitch D, Evans K, Chai D, Duffy K . A highly efficient, asymmetric synthesis of benzothiadiazine-substituted tetramic acids: potent inhibitors of hepatitis C virus RNA-dependent RNA polymerase. Org Lett. 2005; 7(24):5521-4. DOI: 10.1021/ol052371w. View

Liao W, Li S, Wang J, Zhang Z, Yang Z, Xu D . An Efficient and Facile Method for the Synthesis of Benzimidazoisoquinoline Derivatives via a Multicomponent Reaction. ACS Comb Sci. 2015; 18(1):65-9. DOI: 10.1021/acscombsci.5b00145. View

Sunderhaus J, Martin S . Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds. Chemistry. 2009; 15(6):1300-8. PMC: 2803615. DOI: 10.1002/chem.200802140. View

Domling , Ugi I . Multicomponent Reactions with Isocyanides. Angew Chem Int Ed Engl. 2000; 39(18):3168-3210. DOI: 10.1002/1521-3773(20000915)39:18<3168::aid-anie3168>3.0.co;2-u. View

Yang Y, Lu C, Chen M, Chen K, Wu Y, Wu S . Cytotoxic polyketides containing tetramic acid moieties isolated from the fungus Myceliophthora Thermophila: elucidation of the relationship between cytotoxicity and stereoconfiguration. Chemistry. 2007; 13(24):6985-91. DOI: 10.1002/chem.200700038. View

Schreiber S . Target-oriented and diversity-oriented organic synthesis in drug discovery. Science. 2000; 287(5460):1964-9. DOI: 10.1126/science.287.5460.1964. View

Klapper M, Paschold A, Zhang S, Weigel C, Dahse H, Gotze S . Bioactivity and Mode of Action of Bacterial Tetramic Acids. ACS Chem Biol. 2019; 14(8):1693-1697. DOI: 10.1021/acschembio.9b00388. View

Cioc R, Preschel H, van der Heijden G, Ruijter E, Orru R . Trityl Isocyanide as a Mechanistic Probe in Multicomponent Chemistry: Walking the Line between Ugi- and Strecker-type Reactions. Chemistry. 2016; 22(23):7837-42. DOI: 10.1002/chem.201600285. View

10.

Climent M, Corma A, Iborra S . Heterogeneous catalysts for the one-pot synthesis of chemicals and fine chemicals. Chem Rev. 2010; 111(2):1072-133. DOI: 10.1021/cr1002084. View

11.

Li Y, Meng J, Lei J, Chen Z, Tang D, Zhu J . Efficient Synthesis of Fused Oxazepino-isoquinoline Scaffolds via an Ugi, Followed by an Intramolecular Cyclization. ACS Comb Sci. 2017; 19(5):324-330. DOI: 10.1021/acscombsci.7b00002. View

12.

Xu W, Chen M, Wang K, Ren Z, Lu A, Yang C . Synthesis, Characterization, and Antifungal Activity of Phenylpyrrole-Substituted Tetramic Acids Bearing Carbonates. Molecules. 2016; 21(3):355. PMC: 6272832. DOI: 10.3390/molecules21030355. View

13.

Domling A, Wang W, Wang K . Chemistry and biology of multicomponent reactions. Chem Rev. 2012; 112(6):3083-135. PMC: 3712876. DOI: 10.1021/cr100233r. View

14.

Levi L, Muller T . Multicomponent syntheses of functional chromophores. Chem Soc Rev. 2016; 45(10):2825-46. DOI: 10.1039/c5cs00805k. View

15.

Segeth M, Bonnefoy A, Bronstrup M, Knauf M, Schummer D, Toti L . Coniosetin, a novel tetramic acid antibiotic from Coniochaeta ellipsoidea DSM 13856. J Antibiot (Tokyo). 2003; 56(2):114-22. DOI: 10.7164/antibiotics.56.114. View

16.

Marfori E, Kajiyama S, Fukusaki E, Kobayashi A . Phytotoxicity of the tetramic acid metabolite trichosetin. Phytochemistry. 2003; 62(5):715-21. DOI: 10.1016/s0031-9422(02)00629-5. View

17.

Qiu G, Ding Q, Wu J . Recent advances in isocyanide insertion chemistry. Chem Soc Rev. 2013; 42(12):5257-69. DOI: 10.1039/c3cs35507a. View

18.

Schlegel B, Schmidtke M, Dorfelt H, Kleinwachter P, Grafe U . (-)-Terpestacin and L-tenuazonic acid, inducers of pigment and aerial mycelium formation by Fusarium culmorum JP 15. J Basic Microbiol. 2001; 41(3-4):179-83. DOI: 10.1002/1521-4028(200107)41:3/4<179::aid-jobm179>3.0.co;2-h. View

19.

Schobert R, Schlenk A . Tetramic and tetronic acids: an update on new derivatives and biological aspects. Bioorg Med Chem. 2008; 16(8):4203-21. DOI: 10.1016/j.bmc.2008.02.069. View

20.

Hayashi Y . Pot economy and one-pot synthesis. Chem Sci. 2017; 7(2):866-880. PMC: 5529999. DOI: 10.1039/c5sc02913a. View