Popovics-Tóth Nóra, Szabó Kármen Emőke, Bálint Erika
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary.
Materials (Basel). 2021 Oct 13;14(20):6015. doi: 10.3390/ma14206015.
New, practical approaches for the synthesis of α-amino (2-alkynylphenyl)-methylphosphonates and 1,2-dihydroisoquinolin-1-ylphosphonates were developed. By the propylphosphonic anhydride (TP)-mediated Kabachnik-Fields reaction of 2-alkynylbenzaldehydes, aniline, and dialkyl phosphites, α-amino (2-alkynylphenyl)-methylphosphonates were obtained selectively in high yields. The method developed is a simple operation and did not require a chromatographic separation since the products could be isolated from the reaction mixture by a simple extraction. At the same time, 2,3-disubstituted-1,2-dihydroisoquinolin-1-ylphosphonates could be prepared effectively from the same kinds of starting materials (2-alkynylbenzaldehydes, aniline, and dialkyl phosphites) at 60 °C in a short reaction time by changing the catalyst for CuCl. Therefore, it was proved that the catalyst system applied played a crucial role with respect to the reaction outcome.
开发了合成α-氨基（2-炔基苯基）-甲基膦酸酯和1,2-二氢异喹啉-1-基膦酸酯的新型实用方法。通过丙基膦酸酐（TP）介导的2-炔基苯甲醛、苯胺和亚磷酸二烷基酯的卡巴契尼克-菲尔德反应，以高产率选择性地获得了α-氨基（2-炔基苯基）-甲基膦酸酯。所开发的方法操作简单，不需要色谱分离，因为产物可以通过简单萃取从反应混合物中分离出来。同时，通过将催化剂换成CuCl，在60℃下短反应时间内，由相同种类的起始原料（2-炔基苯甲醛、苯胺和亚磷酸二烷基酯）可以有效地制备2,3-二取代-1,2-二氢异喹啉-1-基膦酸酯。因此，证明了所应用的催化剂体系对反应结果起着关键作用。
