Synthesis of Building Blocks for the Construction of Trialomethylated Heterocycles

Synthesis of Building Blocks for the Construction of Trialomethylated Heterocycles

Bencke, Carlos E.; Marangoni, Mário A.; Fortes, Andressa S.; Fantinel, Cássio de A.; Bonacorso, Hélio G.; Martins, Marcos A. P.; Zanatta, Nilo

Abstract:

Many trifluoromethylated heterocycles showing remarkable biological activity have been widely used in a variety of fields ranging from medicine to agricultural products, besides of being versatile intermediate for the synthesis of biologically active compounds containing trifluoromethyl groups. Among these trifluorinated compounds, stand pyridines, which have some approaches to preparation. The general procedures for synthesis of trifluoromethyl-pyridines are generally antimony catalysts, or MoF6 at high temperature and pressure. An alternative method involves direct introduction of trifluoromethyl groups in pyridine, using CF3I or CF3Cl. However, these methods have some disadvantages such as high temperature and pressure, use of HF, low reactivity, low selectivity, limited scope and formation of sub products. Thus, the development of synthetic methods for preparation of trifluoromethylpyridines and other heterocycles, it is highly desired. In this context, the use of simple trifluoromethyl building blocks has often proved to be a better choice than the direct trialomethylation methods. Therefore, this work aims to developing an efficient methodology for the synthesis of convenient trialomethylated building blocks that will be used for the preparation of trialomethylated heterocycles.

Many trifluoromethylated heterocycles showing remarkable biological activity have been widely used in a variety of fields ranging from medicine to agricultural products, besides of being versatile intermediate for the synthesis of biologically active compounds containing trifluoromethyl groups. Among these trifluorinated compounds, stand pyridines, which have some approaches to preparation. The general procedures for synthesis of trifluoromethyl-pyridines are generally antimony catalysts, or MoF6 at high temperature and pressure. An alternative method involves direct introduction of trifluoromethyl groups in pyridine, using CF3I or CF3Cl. However, these methods have some disadvantages such as high temperature and pressure, use of HF, low reactivity, low selectivity, limited scope and formation of sub products. Thus, the development of synthetic methods for preparation of trifluoromethylpyridines and other heterocycles, it is highly desired. In this context, the use of simple trifluoromethyl building blocks has often proved to be a better choice than the direct trialomethylation methods. Therefore, this work aims to developing an efficient methodology for the synthesis of convenient trialomethylated building blocks that will be used for the preparation of trialomethylated heterocycles.

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DOI: 10.5151/chempro-14bmos-R0036-1

Referências bibliográficas

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Como citar:

Bencke, Carlos E.; Marangoni, Mário A.; Fortes, Andressa S.; Fantinel, Cássio de A.; Bonacorso, Hélio G.; Martins, Marcos A. P.; Zanatta, Nilo; "Synthesis of Building Blocks for the Construction of Trialomethylated Heterocycles", p-36-36. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0036-1