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Synthesis 2017; 49(24): 5371-5379
DOI: 10.1055/s-0036-1591310
DOI: 10.1055/s-0036-1591310
paper
New Efficient Synthesis of 2-Thioxo-2,3-dihydropyrimidin-4(1H)-ones from Baylis–Hillman Adducts
This work was financially supported by the Fundamental Research Funds of Central Universities, Southwest University for Nationalities (No. 13NZYBS05), and the Research projects Sichuan Provincial Department of Education (No. 16ZB0028).Further Information
Publication History
Received: 19 July 2017
Accepted after revision: 31 August 2017
Publication Date:
12 October 2017 (online)
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)-onesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591310.
- Supporting Information
- CIF File
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