A New Modification of the Pomeranz-Fritsch Reaction

A New Modification of the Pomeranz-Fritsch Reaction

Naciuk, Fabrício Fredo; Milan, Julio Cesar; Miranda, and Paulo

Abstract:

Pomeranz-Fritsch reaction is a well known strategy to generate isoquinoline nucleus, despite its drawbacks. It is a substrate dependent reaction and alkoxylated substrates may react in particular ways producing undesired products. Depending on alkoxy group position cyclization rate is reduced and intermolecular reactions, solvolysis or ether deprotection begin to occur. Some modifications of the original procedure were introduced in the past by Bobbit and Jackson but, although they improved the yield for most of substrates, these variants still show dependence on pattern substitution.

Pomeranz-Fritsch reaction is a well known strategy to generate isoquinoline nucleus, despite its drawbacks. It is a substrate dependent reaction and alkoxylated substrates may react in particular ways producing undesired products. Depending on alkoxy group position cyclization rate is reduced and intermolecular reactions, solvolysis or ether deprotection begin to occur. Some modifications of the original procedure were introduced in the past by Bobbit and Jackson but, although they improved the yield for most of substrates, these variants still show dependence on pattern substitution.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0257-1

Referências bibliográficas

• [1] 1 Bobbit, J. M.; Kiely, J. M.; Khana, K. L; Ebermann, R. J. Org. Chem. 1965, 30, 2247.
• [2] 2 Birch, A. J.; Jackson, A. H.; Shannon, P. V. R. J. Chem. Soc., Perkin Trans 1 1974, 2185.
• [3] 3 Bianchi, D. A.; Cipulli, M. A.; Kaufman, T. S. Eur. J. Org. Chem. 2003, 4731.
• [4] 4 Armengol, M.; Helliwell, M.; Joule, J. A. Arkivoc 2000, v, 832.
• [5] 5 Li, J.; Kung, D. W.; Griffith, D. A. Tetrahedron Lett. 2010, 51, 3876.

Como citar:

Naciuk, Fabrício Fredo; Milan, Julio Cesar; Miranda, and Paulo; "A New Modification of the Pomeranz-Fritsch Reaction", p-257-257. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0257-1