Synthesis of 2,5-diaryloxazoles Through Rhodium-catalyzed Annulation of Triazoles and Aldehydes

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 May 6

PMID 35517461

Authors

Jian Li

Shang-Rong Zhu

Yue Xu

Xue-Chen Lu

Zheng-Bing Wang

Li Liu

De-Feng Xu

Affiliations

Soon will be listed here.

Abstract

An efficient synthesis of a variety of 2,5-diaryloxazole derivatives a rhodium-catalyzed annulation of triazoles and aldehydes is achieved. Various oxazole derivatives could be obtained in good to excellent yields. A concise synthesis of antimycobaterial natural products balsoxin and texamine has been achieved using this method.

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References

Kolb H, Finn M, Sharpless K . Click Chemistry: Diverse Chemical Function from a Few Good Reactions. Angew Chem Int Ed Engl. 2001; 40(11):2004-2021. DOI: 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5. View

Yu X, Chen K, Wang Q, Zhang W, Zhu J . Synthesis of 2,5-disubstituted oxazoles via cobalt(iii)-catalyzed cross-coupling of N-pivaloyloxyamides and alkynes. Chem Commun (Camb). 2018; 54(10):1197-1200. DOI: 10.1039/c7cc08611c. View

Jiang Y, Sun R, Tang X, Shi M . Recent Advances in the Synthesis of Heterocycles and Related Substances Based on α-Imino Rhodium Carbene Complexes Derived from N-Sulfonyl-1,2,3-triazoles. Chemistry. 2016; 22(50):17910-17924. DOI: 10.1002/chem.201601703. View

Miura T, Yamauchi M, Murakami M . Nickel-catalysed denitrogenative alkyne insertion reactions of N-sulfonyl-1,2,3-triazoles. Chem Commun (Camb). 2009; (12):1470-1. DOI: 10.1039/b819162j. View

Liu L, Bai S, Li Y, Wang L, Hu Y, Sung H . Synthesis of 2,3-Diarylisoindolin-1-one by Copper-Catalyzed Cascade Annulation of 2-Formylbenzonitriles, Arenes, and Diaryliodonium Salts. J Org Chem. 2017; 82(20):11084-11090. DOI: 10.1021/acs.joc.7b02035. View

Miura T, Funakoshi Y, Murakami M . Intramolecular dearomatizing [3 + 2] annulation of α-imino carbenoids with aryl rings furnishing 3,4-fused indole skeletons. J Am Chem Soc. 2014; 136(6):2272-5. DOI: 10.1021/ja412663a. View

Schultz E, Sarpong R . Application of in situ-generated Rh-bound trimethylenemethane variants to the synthesis of 3,4-fused pyrroles. J Am Chem Soc. 2013; 135(12):4696-9. DOI: 10.1021/ja401380d. View

Horneff T, Chuprakov S, Chernyak N, Gevorgyan V, Fokin V . Rhodium-catalyzed transannulation of 1,2,3-triazoles with nitriles. J Am Chem Soc. 2008; 130(45):14972-4. PMC: 2668606. DOI: 10.1021/ja805079v. View

Xu Z, Zhang C, Jiao N . Synthesis of oxazoles through copper-mediated aerobic oxidative dehydrogenative annulation and oxygenation of aldehydes and amines. Angew Chem Int Ed Engl. 2012; 51(45):11367-70. DOI: 10.1002/anie.201206382. View

10.

Spangler J, Davies H . Catalytic asymmetric synthesis of pyrroloindolines via a rhodium(II)-catalyzed annulation of indoles. J Am Chem Soc. 2013; 135(18):6802-5. DOI: 10.1021/ja4025337. View

11.

Jin Z . Muscarine, imidazole, oxazole, and thiazole alkaloids. Nat Prod Rep. 2011; 28(6):1143-91. DOI: 10.1039/c0np00074d. View

12.

Momose Y, Maekawa T, Yamano T, Kawada M, Odaka H, Ikeda H . Novel 5-substituted 2,4-thiazolidinedione and 2,4-oxazolidinedione derivatives as insulin sensitizers with antidiabetic activities. J Med Chem. 2002; 45(7):1518-34. DOI: 10.1021/jm010490l. View

13.

Davies H, Alford J . Reactions of metallocarbenes derived from N-sulfonyl-1,2,3-triazoles. Chem Soc Rev. 2014; 43(15):5151-62. DOI: 10.1039/c4cs00072b. View

14.

Zibinsky M, Fokin V . Sulfonyl-1,2,3-triazoles: convenient synthones for heterocyclic compounds. Angew Chem Int Ed Engl. 2012; 52(5):1507-10. DOI: 10.1002/anie.201206388. View

15.

Gao W, Wang R, Zhang C . Practical oxazole synthesis mediated by iodine from α-bromoketones and benzylamine derivatives. Org Biomol Chem. 2013; 11(41):7123-8. DOI: 10.1039/c3ob41566j. View

16.

Nicolaou K, Hao J, Reddy M, Rao P, Rassias G, Snyder S . Chemistry and biology of diazonamide A: second total synthesis and biological investigations. J Am Chem Soc. 2004; 126(40):12897-906. DOI: 10.1021/ja040093a. View

17.

Miura T, Hiraga K, Biyajima T, Nakamuro T, Murakami M . Regiocontrolled synthesis of polysubstituted pyrroles starting from terminal alkynes, sulfonyl azides, and allenes. Org Lett. 2013; 15(13):3298-301. DOI: 10.1021/ol401340u. View

18.

Mei M, Anand D, Zhou L . Divergent Conversion of N-Acyl-isoxazol-5(2 H)-ones to Oxazoles and 1,3-Oxazin-6-ones Using Photoredox Catalysis. Org Lett. 2019; 21(10):3548-3553. DOI: 10.1021/acs.orglett.9b00903. View

19.

Zhang J, Ciufolini M . An approach to the bis-oxazole macrocycle of diazonamides. Org Lett. 2010; 13(3):390-3. DOI: 10.1021/ol102678j. View

20.

Shi Y, Gevorgyan V . Intramolecular transannulation of alkynyl triazoles via alkyne-carbene metathesis step: access to fused pyrroles. Org Lett. 2013; 15(20):5394-6. PMC: 3946541. DOI: 10.1021/ol4027655. View