New Efficient Synthesis of 2-Thioxo-2,3-dihydropyrimidin-4(1H)-ones from Baylis–Hillman Adducts

Abstract

Azides obtained from Baylis–Hillman adducts were treated with triphenylphosphine to give the corresponding iminophosphoranes, which reacted with carbon disulfide at 40 °C to produce isothiocyanates. The reaction of these isothiocyanates with primary amines provided thiourea intermediates, which in the presence of potassium carbonate or sodium methoxide were converted into 2-thioxo-2,3-dihydropyrimidin-4(1H)-ones in good yields.

Key words

Baylis–Hillman adducts - iminophosphoranes - isothiocyanates - primary amines - aza-Wittig reaction - 2-thioxo-2,3-dihydropyrimidin-4(1H)-ones

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Azides 4 were prepared according to the published methods, see:
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