Base/Electrophile-Controlled Regioselective Functionalization of 1-Substituted-Indolizines

Base/Electrophile-Controlled Regioselective Functionalization of 1-Substituted-Indolizines

Amaral, Mônica F. Z. J.; Baumgartner, Amanda A.; Clososki, Giuliano C.

Abstract:

The pyridine ring is present in a large amount of important polycyclic compounds. Among these, the indolizines stand out for being cores commonly found in nature (particularly in indolizidine alkaloids), in structure of substances of biological interest and for being the indole isosteres. Because of its importance, the optimization of the existing preparation methods or new development to facilitate the construction of indolizines functionalized is of great interest. Thus, the main objective of this project is to develop a regioselective methodology for the direct metalation of functionalized indolizines using organometallic bases that can tolerate the presence of functional groups on the substrates.

The pyridine ring is present in a large amount of important polycyclic compounds. Among these, the indolizines stand out for being cores commonly found in nature (particularly in indolizidine alkaloids), in structure of substances of biological interest and for being the indole isosteres. Because of its importance, the optimization of the existing preparation methods or new development to facilitate the construction of indolizines functionalized is of great interest. Thus, the main objective of this project is to develop a regioselective methodology for the direct metalation of functionalized indolizines using organometallic bases that can tolerate the presence of functional groups on the substrates.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_2013912181622

Referências bibliográficas

• [1] 1 a) Michael, J. P., Nat. Prod. Rep., 2001, 18, 520. b) Wang, Y. F.; Lu, C.
• [2] H.; Lai, et al. Planta Med. 2003, 69, 1066-1068.
• [3] 2 Clososki, G. C.; Rohbogner, C. J.; Knochel, P. Angew Chem. Int. Ed.,
• [4] 2008, 47, 1503-1507.

Como citar:

Amaral, Mônica F. Z. J.; Baumgartner, Amanda A.; Clososki, Giuliano C.; "Base/Electrophile-Controlled Regioselective Functionalization of 1-Substituted-Indolizines", p-217-217. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_2013912181622