Synthesis of 4-Organochalcogenyl-1-H-1,2,3-Triazoles

Synthesis of 4-Organochalcogenyl-1-H-1,2,3-Triazoles

Leal*(PG), Daiana M.; Manarin, Flávia G.; Stefani, Hélio A.

Abstract:

The main goal of Click Chemistry is to develop reactions with simple conditions, wide in scope, high yields and easy product purification, in small and large scales. Huisgen cycloaddition, or 1,3-dipolar cycloaddition, belongs to this group of reactions, and its used to obtain a range of new five-membered heterocycle rings, including 1,2,3-triazoles, achieved through the cycloaddition of an azide to an alkyne. The synthesis of 1,2,3-triazoles is very important because these substances are only obtained through organic synthesis, they are not found in nature. They also have several applications against many diseases like infections and epilepsy. In this context, parallel to the triazoles, we decided to synthesize products that contain the heterocycle ring and an atom of chalcogen. Organoselenium and organotellurium molecules have a large range of biological activity, and are often used as intermediates in organic synthesis. The goal of this work is the functionalization of the position 4 of the triazole ring, inserting chalcogenes in the structure, and at the end obtain a range of new structure with great possibility of biological activity.

The main goal of Click Chemistry is to develop reactions with simple conditions, wide in scope, high yields and easy product purification, in small and large scales. Huisgen cycloaddition, or 1,3-dipolar cycloaddition, belongs to this group of reactions, and its used to obtain a range of new five-membered heterocycle rings, including 1,2,3-triazoles, achieved through the cycloaddition of an azide to an alkyne. The synthesis of 1,2,3-triazoles is very important because these substances are only obtained through organic synthesis, they are not found in nature. They also have several applications against many diseases like infections and epilepsy. In this context, parallel to the triazoles, we decided to synthesize products that contain the heterocycle ring and an atom of chalcogen. Organoselenium and organotellurium molecules have a large range of biological activity, and are often used as intermediates in organic synthesis. The goal of this work is the functionalization of the position 4 of the triazole ring, inserting chalcogenes in the structure, and at the end obtain a range of new structure with great possibility of biological activity.

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DOI: 10.5151/chempro-14bmos-R0346-1

Referências bibliográficas

• [1] 1Kolb, H.C.; Finn, M.G.; Sharpless, K.B. Angew. Chem. Int. Ed. 2001, 40, 2004.
• [2] 2Lal, S.; Díez-Gonzáles, S. J. Org. Chem. 2011, 76, 2367.
• [3] 3Tornol, C.W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
• [4] 4Harju, K.; Vahermo, M.; Mutikainen, I.; Kauhaluoma, J.Y. J. Comb. Chem. 2003, 5, 826.
• [5] 5Potapov, V.A.; Amosova, S.V. Rus. J. Org. Chem. 2003, 39, 1373.

Como citar:

Leal*(PG), Daiana M.; Manarin, Flávia G.; Stefani, Hélio A.; "Synthesis of 4-Organochalcogenyl-1-H-1,2,3-Triazoles", p-346-346. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0346-1