CeCl3·7H2O catalyzed Clauson-Kaas reaction. Synthesis and derivatization of N-Arylpyrroles

CeCl3·7H2O catalyzed Clauson-Kaas reaction. Synthesis and derivatization of N-Arylpyrroles

Silveira, Claudio C.; Fortes, Margiani P.; Mendes, Samuel R.

Abstract:

Pyrroles are an important class of heterocycles which represents not only useful building blocks in natural product synthesis, but also basic structural units in compounds that exhibit remarkable pharmacological activities. One of the most common methods to synthesize pyrroles is the reaction of 2,5-dimehoxytetrahydrofuran with primary amines under acid catalysis, known as Clauson-Kaas reaction. On the other hand, substituted compounds with a thiocyanate group are important intermediates in organic synthesis because they can easily be transformed into various functional groups of sulfur, as sulfide, thioesters, disulfides, thiols, thiocarbamates, etc. Thus, thiocyanation of pyrroles have great applicability in organic synthesis as a direct pathway to form carbon-sufur bonds in the synthesis of new pyrroles derivatives, as disulfides and 1-aryl-2-(trichloromethylthio)-1H-pyrroles.

Pyrroles are an important class of heterocycles which represents not only useful building blocks in natural product synthesis, but also basic structural units in compounds that exhibit remarkable pharmacological activities. One of the most common methods to synthesize pyrroles is the reaction of 2,5-dimehoxytetrahydrofuran with primary amines under acid catalysis, known as Clauson-Kaas reaction. On the other hand, substituted compounds with a thiocyanate group are important intermediates in organic synthesis because they can easily be transformed into various functional groups of sulfur, as sulfide, thioesters, disulfides, thiols, thiocarbamates, etc. Thus, thiocyanation of pyrroles have great applicability in organic synthesis as a direct pathway to form carbon-sufur bonds in the synthesis of new pyrroles derivatives, as disulfides and 1-aryl-2-(trichloromethylthio)-1H-pyrroles.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0286-1

Referências bibliográficas

• [1] 1 Morales, G. O.; Méndez, F.; Miranda, D. L. Tetrahedron Lett. 2007, 48, 4515; Furstner, A. Angew. Chem. Int. Ed. 2003, 42, 3582; Richards, J. J.; Reed, C. S.; Melander, C. Bioorg. Med. Chem. Lett. 2008, 18, 4325.
• [2] 2 Clauson-Kaas, N.; Tyle, Z. Acta Chem. Scand. 1952, 6, 667; Elming, N.; Clauson-Kaas, N. Acta Chem. Scand. 1952, 6, 867.
• [3] 3 Toste, F. D.; LaRonde, F.; Still, I. W. J. Tetrahedron Lett. 1995, 36, 2949; Pilyugin, V. S.; Sapozhnikov, Y. E.; Shitov, G. P. Russ. J. Org. Chem., 2003, 39, 1040; Tarbell, D. S.; Harnish, D. P. Chem. Rev. 1951, 49, 1.
• [4] 4 Makosza, M.; Fedorynski, M. Synthesis, 1974, 274.

Como citar:

Silveira, Claudio C.; Fortes, Margiani P.; Mendes, Samuel R.; "CeCl3·7H2O catalyzed Clauson-Kaas reaction. Synthesis and derivatization of N-Arylpyrroles", p-286-286. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0286-1