The multicomponent Hantzsch reaction: comprehensive mass spectrometry monitoring using charge-tagged reagents

Chemistry. 2014 Sep 26;20(40):12808-16. doi: 10.1002/chem.201303065. Epub 2014 Sep 1.

Abstract

A novel strategy for the ESI-MS monitoring of reaction solutions involving the alternate use of permanently charge-tagged reagents has been used for comprehensive mass spectrometry monitoring of the multicomponent Hantzsch 1,4-dihydropyridine reaction. By placing a charge tag on either, or both, of the two key reactants, ion suppression effects for ESI were eliminated or minimized, and comprehensive detection of charge-tagged intermediates was achieved. The strategy allowed the trapping and characterization of the important intermediates in the mechanism for 1,4-dihydropyridine formation.

Keywords: charge tags; electrospray ionization; ionic intermediates; multicomponent reactions; reaction mechanisms.