Ritter reaction of N-(hydroxymethyl)saccharin with nitriles: synthesis of new N-(amidomethyl)saccharins

Ritter reaction of N-(hydroxymethyl)saccharin with nitriles: synthesis of new N-(amidomethyl)saccharins

Mattos, Marllon N. de Oliveira e Marcio C. S. de

Abstract:

Considerable interest has been focused on saccharin derivatives which have been shown to possess a broad spectrum of biological activities, such as fungicidal, antibacterial, and antiinflammatory effects. The Ritter reaction, first reported in 1948, allows the formation of amides and it is particularly useful for the preparation of bulky products. In this reaction, a carbocation generated in situ from an alcohol, an alcohol derivative, or an olefin is trapped by a nitrile to produce a nitrilium species, which after hydrolysis produces an amide. In the case of alcohols, the substrate itself generates H2O and the process becomes atom-economical. Other reactions in which a carbocation generated in situ is trapped by nitrile are referred to as Ritter-type reactions. Thus, it was proposed to prepare new drug candidates through the Ritter reaction, by analogy to the work of Buc, condensing N-(hydroxymethyl)- saccharin with nitriles.

Considerable interest has been focused on saccharin derivatives which have been shown to possess a broad spectrum of biological activities, such as fungicidal, antibacterial, and antiinflammatory effects. The Ritter reaction, first reported in 1948, allows the formation of amides and it is particularly useful for the preparation of bulky products. In this reaction, a carbocation generated in situ from an alcohol, an alcohol derivative, or an olefin is trapped by a nitrile to produce a nitrilium species, which after hydrolysis produces an amide. In the case of alcohols, the substrate itself generates H2O and the process becomes atom-economical. Other reactions in which a carbocation generated in situ is trapped by nitrile are referred to as Ritter-type reactions. Thus, it was proposed to prepare new drug candidates through the Ritter reaction, by analogy to the work of Buc, condensing N-(hydroxymethyl)- saccharin with nitriles.

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013715124551

Referências bibliográficas

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Como citar:

Mattos, Marllon N. de Oliveira e Marcio C. S. de; "Ritter reaction of N-(hydroxymethyl)saccharin with nitriles: synthesis of new N-(amidomethyl)saccharins", p-146-146. 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_2013715124551