Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.



Development of a telescoped synthesis of 4-(1H)-cyanoimidazole core accelerated by orthogonal reaction monitoring

Author affiliations

Abstract

We have developed a convenient two-step, one-pot method for the facile synthesis of cyanoimidazoles. By integrating a suite of reaction-monitoring techniques, we were able to interrogate each transformation independently. We observed that formation of a key hemiaminal intermediate is complicated via many equilibrium processes, creating oligomers and eventually resulting in unproductive dimerization. DoE experiments indicated that despite the complex equilibria of this substrate, high conversion to the trifluoromethyl imidazole can still be achieved. We also report the effects of temperature, pH, and substrate concentrations on the rate and selectivity of the elimination cascade reaction converting the trifluoromethyl imidazole to the cyanoimidazole. By leveraging kinetic information gathered from each step independently, we report reaction conditions to achieve high yields of the cyanoimidazole from carbonyl-containing substrate directly in one pot.

Graphical abstract: Development of a telescoped synthesis of 4-(1H)-cyanoimidazole core accelerated by orthogonal reaction monitoring

Back to tab navigation

Supplementary files

Article information


Submitted
03 Jun 2020
Accepted
21 Jun 2020
First published
22 Jun 2020

React. Chem. Eng., 2020, Advance Article
Article type
Paper

Development of a telescoped synthesis of 4-(1H)-cyanoimidazole core accelerated by orthogonal reaction monitoring

T. C. Malig, Y. Tan, S. R. Wisniewski, C. S. Higman, R. Carrasquillo-Flores, A. Ortiz, G. E. Purdum, S. Kolotuchin and J. E. Hein, React. Chem. Eng., 2020, Advance Article , DOI: 10.1039/D0RE00234H

Social activity

Search articles by author

Spotlight

Advertisements