Recent development of Silver-catalyzed Oxo- and Aza cyclization

Swapan Kumar Biswas

doi:10.52756/ijerr.2021.v26.007

Authors

Swapan Kumar Biswas Department of Chemistry, Sree Chaitanya College, Habra, North 24 Parganas, West Bengal, India https://orcid.org/0000-0002-2757-7702

DOI:

https://doi.org/10.52756/ijerr.2021.v26.007

Keywords:

Aza cyclization, oxo cyclization, silver-catalyzed, pyran, pyrroles

Abstract

This article addresses new developments in silver-catalyzed cyclization processes, resulting in the formation of carbocyclic or heterocyclic rings. Some essential techniques in organic chemistry include silver-catalyzed reactions. In addition, silver catalysts have been emerged as a novel catalysis in the last two decades. In these sequences, preparations of oxygen and nitrogen-containing heterocyclic compounds emerge as the most important development of new methodology. Silver catalysts exhibit significant reactivity in mild conditions in contrast to other transition metals such as copper, lead, zinc, ruthenium, gallium, indium, and niobium. These developments have lots of scientific attention due to their potential to synthesise of heterocyclic compounds in medicinal and agrochemical use. This current literature review summarises several silver-catalyzed oxo and aza-cyclization processes using readily available starting materials.

References

Akkachairin, B., Tummatorn, J., Supantanapong, N., Nimnual, P., Thongsornkleeb, C. and Ruchirawat, S. (2017). Silver-Catalyzed Cyclization of Carbonylarylacetylenols for the Synthesis of Dihydronaphthofurans. The Journal of Organic Chemistry. 82(7): 3727–3740.

Bai, X., Zhang, J., Xia, C., Xu, J. and Xu, L. (2016). N-tert-Butanesulfinyl imine and aromatic tertiary amide derived non-biaryl atropisomers as chiral ligands for silver-catalyzed endo-selective [3+2] cycloaddition of azomethine ylides with maleimides. Tetrahedron. 72(21): 2690-2699.

Cao, Z., Zhu, H., Meng, X., Tian, L., Chen, G., Sun, X. and You, J. (2016). Silver-Catalyzed Domino Reaction of ortho-Carbonylated Alkynyl-Substituted Arylaldehydes with Conjugated Dienes: Stereoselective Access to Indanone-Fused Cyclohexenes. The Journal of Organic Chemistry. 81(24): 12401–12407.

Kitagaki, S., Teramoto, S. and Mukai, C. (2007). Ring-Closing Reaction of Allenic/Propargylic Anions Generated by Base Treatment of Sulfonylallenes. Organic Letters. 9: 2549−2552.

Kazuhiro, W., Jinming. Li., Nagarathanam. V., Ghosh, A. and Carter, R. G. (2016). Stereoselective, Ag-Catalyzed Cyclizations To Access Polysubstituted Pyran Ring Systems: Synthesis of C1-C2 Subunit of Madeirolide A. Organic Letters. 18(8): 1744–1747.

Liu, R., Shan, Q., Gao, Y., Loh, T. and Hu, X. (2021). Access to multi-functionalized oxazolines via silver-catalyzed heteroannulation of enamides with sulfoxonium ylides. Chinese Chemical Letters. 32(4): 1411-1414.

Liu, Y., Hu, H., Wang, X., Zhi, S., Kan, Y. and Wang, C. (2017). Synthesis of Pyrrole via a Silver-Catalyzed 1,3-Dipolar Cycloaddition/Oxidative Dehydrogenative Aromatization Tandem Reaction. The Journal of Organic Chemistry. 82(8): 4194–4202.

Mukai, C., Ohta, M., Yamashita, H. and Kitagaki, S. (2004). Base-Catalyzed Endo-Mode Cyclization of Allenes: Easy Preparation of Five- to Nine-Membered Oxacycles. The Journal of Organic Chemistry. 69(20): 6867−6873.

Sinha, D., Biswas, A. and Singh, V. K. (2015). Chiral Phosphine–Silver (I) Complex Catalyzed Enantioselective Interrupted Feist–Bénary Reaction with Ynones: The Aldol–Cycloisomerization Cascade. Organic Letters. 17(13): 3302–3305.

Tata, R. R. and Michael, H. (2016). Silver-Catalyzed Cyclization of Sulfonyl Allenes to Dihydrofurans. Organic Letters. 18(21): 5684–5687.

Wei W, Shunli W, Xinyu Z, Qi L. and Zhiqiang W.* (2021). Silver-Catalyzed Regioselective Synthesis of Highly Substituted 2-Trifluoromethyl Pyrroles. Organic Letters. 23(16): 6352–6356.

Yadav, J. S., Reddy, B.V.S., Eeshwaraiah, B., Gupta, M.K. and Biswas. S. K. (2005). Gallium (III) halide promoted synthesis of 1, 3, 5-triaryl-1, 5-dihalo-1, 4-pentadienes. Tetrahedron letters. 46 (7): 1161-1163.

Yadav, J. S., Reddy, B.V.S, Biswas, S. K. and Sengupta, S. (2009). Gallium (III) chloride-catalyzed three-component coupling of naphthol, alkyne and aldehyde: a novel synthesis of 1, 3-disubstituted-3H-benzo [f] chromenes. Tetrahedron Letters. 50 (42): 5798-5801.

Yadav, J. S., Reddy, B.V.S, Sengupta, S. and Biswas, S. K. (2009). Gallium (III) chloride catalyzed hydroarylation of arylacetylenes with naphthols and phenols: a facile synthesis of vinylarenes. Synthesis. 40(37): 1301-1304.

Yadav, J. S., Reddy, B.V.S, Biswas, S. K., Vishnumurthy, P. (2007). Indium-mediated allylation/propargylation of α-diazoketones: a facile synthesis of 1-bromo-2-alkyl-or 2-arylpent-4-en-2-ols. Tetrahedron Letters. 48 (38): 6641-66432.

Yadav, J. S., Reddy, B.V.S, Gupta, M. K. and Biswas, S. K. (2004). Rapid and efficient protocol for the synthesis of 4-chlorotetrahydropyrans using Niobium (V) Chloride. Synthesis. (16): 2711-2715.

Yadav, J. S., Reddy, B.V.S, Biswas, S. K., Sengupta, S., Vishnumurthy, V. (2008). Indium-mediated vic-diallylation/propargylation of phenacyl bromides: a facile synthesis of 4-arylocta-1, 7-dien-4-ol derivatives. Tetrahedron Letters. 49 (6): 1034-1036.