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Iron(III)-catalyzed selective direct olefination of dihydropyrimidinone with aromatic aldehyde

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Abstract

Herein, we describe a practical approach for direct vinylogous aldol condensation of Biginelli product for carbon–carbon double bond formation at methyl group of 6-methyl dihydropirimidinone by using hydrated ferric chloride. With aromatic aldehydes, the method yields stereoselectively trans products. The olefination reaction is applicable with aldehyde without chelating (with Fe III) functional group. DHPMs with carboxylate ester and arylidene at C-6 methyl are not known. The method opens up a new avenue for the synthesis of a wide variety of DHPMs. The olefin products were subjected to dihydroxylation reaction.

Graphical Abstract

SYNOPSIS A convenient and facile C6-olefination at methyl centre of dihydropyrimidinones (DHPMs) has been observed in acetonitrile in the presence of hydrated \(\hbox {FeCl}_{3}\). The method is simple, inexpensive, and stereoselectively trans.

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Acknowledgements

We thank the SERB New Delhi, for financial support under EMR scheme (EMR/2014/000542).

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Authors and Affiliations

  1. Department of Chemistry, Jadavpur University, Kolkata, West Bengal, 700 032, India

    Mohabul A Mondal

  2. Department of Chemistry, University of Gour Banga, Malda, West Bengal, 732 103, India

    Mohabul A Mondal, Abdul Ashik Khan & Kanchan Mitra

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  1. Mohabul A Mondal
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Correspondence to Mohabul A Mondal.

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Mondal, M.A., Khan, A.A. & Mitra, K. Iron(III)-catalyzed selective direct olefination of dihydropyrimidinone with aromatic aldehyde. J Chem Sci 130, 151 (2018). https://doi.org/10.1007/s12039-018-1543-z

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