Regioselective Synthesis of 3-Haloalkyl-isoxazoles from the Electrophilic Cyclization of Halogenated Oximes

Regioselective Synthesis of 3-Haloalkyl-isoxazoles from the Electrophilic Cyclization of Halogenated Oximes

Amaral, Simone Schneider; Schneider, Paulo Henrique

Abstract:

Heterocycles constitute a major group of organic compounds. Among the great variety of existing heterocycles, the isoxazole core stands out due to its synthetic versatility and broad spectrum of interesting biological activities. Additionally, the development of new strategies for synthesizing halogenated heterocycles has received much attention since the presence of such groups is often associated with improvements in pharmacological properties of organic molecules. From a synthetic perspective, the regio and stereoselective control for the introduction of haloalkyl substituents in heterocycles is limited. Therefore, efficient and simple methods for the straightforward synthesis of haloalkyl-isoxazoles are highly desired.

Heterocycles constitute a major group of organic compounds. Among the great variety of existing heterocycles, the isoxazole core stands out due to its synthetic versatility and broad spectrum of interesting biological activities. Additionally, the development of new strategies for synthesizing halogenated heterocycles has received much attention since the presence of such groups is often associated with improvements in pharmacological properties of organic molecules. From a synthetic perspective, the regio and stereoselective control for the introduction of haloalkyl substituents in heterocycles is limited. Therefore, efficient and simple methods for the straightforward synthesis of haloalkyl-isoxazoles are highly desired.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0053-1

Referências bibliográficas

• [1] 1 (a) Eicher, T.; Hauptmann, S. The Chemistry of Heterocycles – Structure, Reactions, Synthesis, and Applications, Willey-VHC Verlag GmbH and Co. KGaA, 2ª ed. 2003. (b) Taldone, T.; Sun, W.; Chiosis, G, Bioorg. Med. Chem. 2009, 17, 2225.
• [2] 2 Taldone, T.; Sun, W.; Chiosis, G, Bioorg. Med. Chem. 2009, 17, 2225.
• [3] 3 (a) Waldo, J. P.; Larock, R. C. Org. Lett. 2005, 23, 5203. (b) Chen, Y.; Cho, C.-H.; Larock, R. C. Org. Lett. 2009, 11, 173.

Como citar:

Amaral, Simone Schneider; Schneider, Paulo Henrique; "Regioselective Synthesis of 3-Haloalkyl-isoxazoles from the Electrophilic Cyclization of Halogenated Oximes", p-53-53. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0053-1