Abstract
A mild and efficient method catalyzed by α-chymotrypsin was developed for the synthesis of bis(indolyl)methanes through a cascade process between indole and aromatic aldehydes. In the ethanol aqueous solution, a green medium, a wide range of aromatic aldehydes could react with indole to afford the desired products with moderate to good yields (from 68% to 95%) using a little α-chymotrypsin as catalyst.
Highlights
IntroductionBis(indolyl)methane and their derivatives are members of an important class of heterocyclic compounds that display diverse biological properties, and can act as a selective colorimetric sensor for
Bis(indolyl)methane and their derivatives are members of an important class of heterocyclic compounds that display diverse biological properties, and can act as a selective colorimetric sensor forF− and as a highly selective fluorescent molecular sensor for Cu2+ [1,2]
Various methods were mentioned for the synthesis of bis(indolyl)methanes, generally, these compounds could be obtained by the cascade reaction between indole and aromatic aldehydes in the present of protic or Lewis acids, such as I2 [6], Ionic liquids [7], Molecules 2014, 19
Summary
Bis(indolyl)methane and their derivatives are members of an important class of heterocyclic compounds that display diverse biological properties, and can act as a selective colorimetric sensor for. Various methods were mentioned for the synthesis of bis(indolyl)methanes, generally, these compounds could be obtained by the cascade reaction between indole and aromatic (or aliphatic) aldehydes in the present of protic or Lewis acids, such as I2 [6], Ionic liquids [7], Molecules 2014, 19. High selectivity and eco-friendly catalyst for the organic synthesis, enzymes have attracted much attention in the field of synthetic chemistry [18,19,20]. As a part of our continuing interest in green chemistry and enzyme promiscuity, we wish to report the protease-catalyzed cascade reaction between indole and aromatic aldehydes (Scheme 1). Α-chymotrypsin was selected as the biocatalyst, and a series of aromatic aldehydes could react with indole to afford the corresponding bis(indolyl)methanes in ethanol aqueous solution, which was obviously a green synthesis method. Scheme 1. α-Chymotrypsin-catalyzed tandem reaction of indole and aldehydes
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
