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New Efficient Synthesis of 2-Thioxo-2,3-dihydropyrimidin-4(1H)-ones from Baylis–Hillman Adducts
Synthesis ( IF 2.2 ) Pub Date : 2017-10-12 , DOI: 10.1055/s-0036-1591310
Ying Zhong , Zhigang Zhao , Xiuhua Chen , Gang Huang

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.

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.



中文翻译:

从Baylis–Hillman加合物合成2-硫代-2,3-二氢嘧啶-4(1H)-的新有效化合物

摘要

用三苯基膦处理从Baylis-Hillman加合物获得的叠氮化物,得​​到相应的亚氨基正膦,该亚氨基正膦在40°C下与二硫化碳反应生成异硫氰酸酯。这些异硫氰酸酯与伯胺的反应提供了硫脲中间体,该中间体在碳酸钾或甲醇钠存在下以良好的产率转化为2-硫代-2-3,3-二氢嘧啶-4(1H)-一。

用三苯基膦处理从Baylis-Hillman加合物获得的叠氮化物,得​​到相应的亚氨基正膦,该亚氨基正膦在40°C下与二硫化碳反应生成异硫氰酸酯。这些异硫氰酸酯与伯胺的反应提供了硫脲中间体,该中间体在碳酸钾或甲醇钠存在下以良好的产率转化为2-硫代-2-3,3-二氢嘧啶-4(1H)-一。

更新日期:2017-10-12
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