An improved solvent-free procedure for synthesis of bis(indolyl)methanes

An improved solvent-free procedure for synthesis of bis(indolyl)methanes

Mendes, Samuel R.; Thurow, Samuel; Fortes, Margiani P.; Lenardão, Eder J.; Alves, Diego; Perin, Gelson; Jacob, Raquel G.

Abstract:

Indoles and their derivatives are widely present in bioactive metabolites of compounds of both terrestrial and marine origin. The bis(indolyl)methane (BIM) of simpler structure, bis(3- indolyl)methane, Figure 1, has recently been used as chemotherapy in cancer treatment. Because of BIM’s versatile biological activities, in particular the pharmacological one, various methods are mentioned for their preparation. A drawback of most of the described methods is the use of expensive and toxic reagents and volatile solvents. In this work, because of our interest in the development of new efficient and green methodologies, we decided to study the electrophilic substitution reaction of indoles with carbonyl compounds to obtain bis(indolyl)methanes using silica gel as recyclabe catalyst.

Indoles and their derivatives are widely present in bioactive metabolites of compounds of both terrestrial and marine origin. The bis(indolyl)methane (BIM) of simpler structure, bis(3- indolyl)methane, Figure 1, has recently been used as chemotherapy in cancer treatment. Because of BIM’s versatile biological activities, in particular the pharmacological one, various methods are mentioned for their preparation. A drawback of most of the described methods is the use of expensive and toxic reagents and volatile solvents. In this work, because of our interest in the development of new efficient and green methodologies, we decided to study the electrophilic substitution reaction of indoles with carbonyl compounds to obtain bis(indolyl)methanes using silica gel as recyclabe catalyst.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0143-1

Referências bibliográficas

• [1] 1 Sundberg, R. J. Indoles; Academic Press: San Diego, 1996.
• [2] 2 Safe, S.; Papineni, S.; Chintharlapalli, S. Cancer Lett. 2008, 269, 326.
• [3] 3 Nagarajan R.; Perumal, P. T. Tetrahedron 2002, 58, 1229; Chakrabarty, M.; Ghosh, N.; Basak, R.; Harigaya, Y. Tetrahedron Lett. 2002, 43, 4075; Chen, D.; Yu, L.; Wang, P. G. Tetrahedron Lett. 1996, 37, 4467; Deb, M.
• [4] L.; Bhuyan, P. J. Synlett 2008, 325; Shiri, M.; Zolfigol, M. A.; Kruger, H. G.; Tanbakouchian, Z. Chem. Rev. 2010, 110, 2250.

Como citar:

Mendes, Samuel R.; Thurow, Samuel; Fortes, Margiani P.; Lenardão, Eder J.; Alves, Diego; Perin, Gelson; Jacob, Raquel G.; "An improved solvent-free procedure for synthesis of bis(indolyl)methanes", p-143-143. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0143-1