A convenient synthesis of bis(indolyl)methane derivatives using heteroaromatic isocyanurate ring functionalized MCM-41 as a new and highly efficient reusable catalyst

Indole frameworks or scaffold are the most heterocyclic compounds in many biological systems that show medicinal properties and pharmacological activity.¹ During the past, a large numeral of natural products containing bis(indolyl)methanes (BIM’s), which contain two indole or substituted indole units in a molecule, have been isolated from marine sources. The BIM’s exhibit antibacterial, antibiotics, analgesic and anti-inflammatory activities. They are also highly beneficial in promoting good estrogen and increase the body’s natural metabolism of hormones.^2,3

In continuing to our ongoing efforts towards developing efficient catalysts for different MCRs ^4,5, we report herein heteroaromatic isocyanurate ring functionalized MCM-41, as a new, efficient and recoverable catalyst, for the synthesis of BIM derivatives (Scheme 1).

­ Scheme 1. Representative examples of biologically active bisindolylmethane (BIM) derivatives.

References

(1) Shiri, M. Chemical reviews 2012, 112, 3508.

(2) Sarva, S.; Harinath, J. S.; Sthanikam, S. P.; Ethiraj, S.; Vaithiyalingam, M.; Cirandur, S. R. Chinese Chemical Letters 2016, 27, 16.

(3) Yaghoubi, A.; Dekamin, M. G.; Arefi, E.; Karimi, B. Journal of Colloid and Interface Science 2017, 505, 956.

(4) Dekamin, M. G.; Azimoshan, M.; Ramezani, L. Green Chemistry 2013, 15, 811.

(5) Dekamin, M. G.; Kazemi, E.; Karimi, Z.; Mohammadalipoor, M.; Naimi-Jamal, M. R. International journal of biological macromolecules 2016, 93, 767.