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Synthesis of 6-styryldihydropyrimidinones and 6-styryldihydropyridinones via the respective 6-alkylphosphonates

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Chemistry of Heterocyclic Compounds Aims and scope

Trimethyl or triethyl phosphite in the Arbuzov reaction with 6-bromomethyl-3,4-dihydropyrimidin-2(1H)-one or analogous 6-bromomethyl-3,4-dihydropyridin-2(1H)-one provided the respective 6-alkylphosphonates in excellent yields. The heterocyclic alkylphosphonates are useful synthons in the Horner–Wadsworth–Emmons reaction for introducing a styryl moiety. Bromination of 6-methyl-4-phenyl-3,4-dihydropyridin-2(1H)-one with NBS in methanol resulted in an unexpected compound, while bromination in chloroform with bromine yielded the expected 6-bromomethyl-3,4-dihydropyridin-2(1H)-one, which undergoes facile nucleophilic substitutions. The intermediates and products are validated by single crystal X-ray diffraction.

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Authors and Affiliations

  1. Latvian Institute of Organic Synthesis, 21 Aizkraukles St, Riga, LV-1006, Latvia

    Rufus Smits, Sergey Belyakov, Marina Petrova & Ruslan Muhamadejev

  2. Riga Stradins University, 16 Dzirciema St, Riga, LV-1007, Latvia

    Vladislav Kozhich

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  1. Rufus Smits
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  2. Sergey Belyakov
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  3. Marina Petrova
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  4. Vladislav Kozhich
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  5. Ruslan Muhamadejev
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Correspondence to Rufus Smits.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(12), 687–694

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Smits, R., Belyakov, S., Petrova, M. et al. Synthesis of 6-styryldihydropyrimidinones and 6-styryldihydropyridinones via the respective 6-alkylphosphonates. Chem Heterocycl Comp 58, 687–694 (2022). https://doi.org/10.1007/s10593-023-03145-7

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