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Issue 11, 2017
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An unexpected acid-catalyzed decomposition reaction of cilnidipine and pranidipine to the decarboxylative bridged tricyclic products via cascade rearrangements

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Abstract

A gas-phase Carroll rearrangement occurring during electrospray ionization tandem mass spectrometry (ESI-MS/MS) led to the discovery of bridged tricyclic degradation products from cilnidipine and pranidipine under acidic conditions for the first time. The unexpected acid-catalyzed decomposition product of cilnidipine was separated and identified by MS, NMR and X-ray analyses. An acid-catalyzed Carroll rearrangement, a hetero-DielsAlder reaction and a sigmatropic rearrangement cascade reaction were proposed for the formation of bridged tricyclic degradation products from cilnidipine and pranidipine under acidic conditions. Theoretical calculations supported the proposed reaction mechanism.

Graphical abstract: An unexpected acid-catalyzed decomposition reaction of cilnidipine and pranidipine to the decarboxylative bridged tricyclic products via cascade rearrangements

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Publication details

The article was received on 21 Jun 2017, accepted on 27 Jul 2017 and first published on 28 Jul 2017


Article type: Research Article
DOI: 10.1039/C7QO00496F
Citation: Org. Chem. Front., 2017,4, 2163-2166
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    An unexpected acid-catalyzed decomposition reaction of cilnidipine and pranidipine to the decarboxylative bridged tricyclic products via cascade rearrangements

    M. Yang, S. Zhang, X. Zhang, H. Wang, F. Zhang, Y. Hou, Y. Su and Y. Guo, Org. Chem. Front., 2017, 4, 2163
    DOI: 10.1039/C7QO00496F

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