Tetrazole Synthesis Via the Palladium-catalyzed Three Component Coupling Reaction

Overview

Journal Mol Divers

Date 2004 Apr 8

PMID 15068080

Citations 4

Authors

Shin Kamijo

Tienan Jin

Zhibao Huo

Young Soo Gyoung

Jae-Goo Shim

Yoshinori Yamamoto

Affiliations

Soon will be listed here.

Abstract

The synthesis of tetrazoles was achieved via the palladium-catalyzed three component coupling (TCC) reaction; The TCC reaction of malononitrile derivatives, allyl acetate and trimethylsilyl azide proceeds very smoothly under a catalytic amount of Pd(PPh3)4 to give 2-allyltetrazoles, and further the TCC reaction of various activated cyano compounds, allyl methyl carbonate and trimethylsilyl azide proceeds readily under a catalytic amount of Pd2(dba)3 x CHCl3 and (2-furyl)3P to give 2-allyltetrazoles. pi-Allylpalladium azide complex is proposed as a key intermediate in the catalytic cycle and the [3 + 2] cycloaddition between the pi-allylpalladium azide complex and cyano compounds most probably gives the tetrazole frameworks. The deallylation of the derived allyltetrazoles was attained via the two-step procedure; the ruthenium-catalyzed isomerization and ozonolysis.

Citing Articles

Catalytic Tetrazole Synthesis via [3+2] Cycloaddition of NaN to Organonitriles Promoted by Co(II)-complex: Isolation and Characterization of a Co(II)-diazido Intermediate.

Babu A, Sinha A ACS Omega. 2024; 9(19):21626-21636.

PMID: 38764698 PMC: 11097157. DOI: 10.1021/acsomega.4c02567.

Design and characterization of an urea-bridged PMO supporting Cu(II) nanoparticles as highly efficient heterogeneous catalyst for synthesis of tetrazole derivatives.

Valiey E, Dekamin M Sci Rep. 2022; 12(1):18139.

PMID: 36307538 PMC: 9616949. DOI: 10.1038/s41598-022-22905-7.

Theoretical investigations on the stability of alkali metal substituted phenylpentazole.

Zhang X, Gong X J Mol Model. 2016; 22(5):106.

PMID: 27083566 DOI: 10.1007/s00894-016-2971-7.

Theoretical investigations on stability of pyridylpentazoles, pyridazylpentazoles, triazinylpentazoles, tetrazinylpentazoles, and pentazinylpentazole searching for a replacement of phenylpentazole as N5 (-) source.

Zhang X, Gong X J Mol Model. 2015; 21(12):318.

PMID: 26615562 DOI: 10.1007/s00894-015-2867-y.

References

Demko Z, Sharpless K . A click chemistry approach to tetrazoles by Huisgen 1,3-dipolar cycloaddition: synthesis of 5-sulfonyl tetrazoles from azides and sulfonyl cyanides. Angew Chem Int Ed Engl. 2009; 41(12):2110-3. View

Demko Z, Sharpless K . Preparation of 5-substituted 1H-tetrazoles from nitriles in water. J Org Chem. 2001; 66(24):7945-50. DOI: 10.1021/jo010635w. View

Ashton W, Cantone C, Chang L, Hutchins S, Strelitz R, MacCoss M . Nonpeptide angiotensin II antagonists derived from 4H-1,2,4-triazoles and 3H-imidazo[1,2-b][1,2,4]triazoles. J Med Chem. 1993; 36(5):591-609. DOI: 10.1021/jm00057a009. View

Alterman , Hallberg . Fast microwave-assisted preparation of aryl and vinyl nitriles and the corresponding tetrazoles from organo-halides. J Org Chem. 2000; 65(23):7984-9. DOI: 10.1021/jo0009954. View

Kamijo S, Yamamoto Y . Synthesis of allyl cyanamides and N-cyanoindoles via the palladium-catalyzed three-component coupling reaction. J Am Chem Soc. 2002; 124(40):11940-5. DOI: 10.1021/ja0272742. View

Kamijo S, Jin T, Yamamoto Y . Novel synthetic route to allyl cyanamides: palladium-catalyzed coupling of isocyanides, allyl carbonate, and trimethylsilyl azide. J Am Chem Soc. 2001; 123(38):9453-4. DOI: 10.1021/ja016355f. View

Bovy P, Reitz D, Collins J, Chamberlain T, Olins G, Corpus V . Nonpeptide angiotensin II antagonists: N-phenyl-1H-pyrrole derivatives are angiotensin II receptor antagonists. J Med Chem. 1993; 36(1):101-10. DOI: 10.1021/jm00053a013. View

Demko Z, Sharpless K . A click chemistry approach to tetrazoles by Huisgen 1,3-dipolar cycloaddition: synthesis of 5-acyltetrazoles from azides and acyl cyanides. Angew Chem Int Ed Engl. 2009; 41(12):2113-6. View

Singh H, Chawla A, Kapoor V, Paul D, Malhotra R . Medicinal chemistry of tetrazoles. Prog Med Chem. 1980; 17:151-83. DOI: 10.1016/s0079-6468(08)70159-0. View

10.

Batey R, Powell D . A general synthetic method for the formation of substituted 5-aminotetrazoles from thioureas: a strategy for diversity amplification. Org Lett. 2000; 2(20):3237-40. DOI: 10.1021/ol006465b. View

11.

Marshall W, Goodson T, Cullinan G, Haisch K, Rinkema L, Fleisch J . Leukotriene receptor antagonists. 1. Synthesis and structure-activity relationships of alkoxyacetophenone derivatives. J Med Chem. 1987; 30(4):682-9. DOI: 10.1021/jm00387a018. View

12.

Kamijo S, Jin T, Yamamoto Y . Palladium-catalyzed selective synthesis of 2-allyltetrazoles. J Org Chem. 2002; 67(21):7413-7. DOI: 10.1021/jo026147l. View

13.

Demko Z, Sharpless K . An intramolecular [2 + 3] cycloaddition route to fused 5-heterosubstituted tetrazoles. Org Lett. 2001; 3(25):4091-4. DOI: 10.1021/ol010220x. View