Synthesis of Amidophosphates Based on 1-Ethynyl-1-Aminocyclohexane Upon Microwave Activation and their Biological Activity
Dzhiembaev B.J. Kuandykova A.B. Akylbekov N.I. Dobrynin A. Burilov A.R.
20 March 2023Institute of Combustion Problems, al-Farabi Kazakh State National University
Eurasian Chemico-Technological Journal
2023#25Issue 157 - 64 pp.
The researches for developing the methods for synthesizing new functionally substituted derivatives of alicyclic dialkylamidophosphates, establishing their structure, and searching for promising biologically active compounds in their series, are modern and relevant. The given study aimed to develop the synthesis of amidophosphates based on the example of phosphorylation of 1-ethynyl-1-aminocyclohexane with dialkyl phosphites in the presence of triethylamine in carbon tetrachloride in the Atherton-Todd reaction conditions using microwave irradiation of the reaction mixture. The reaction of 1-ethynyl-1-aminocyclohexane with dialkyl phosphites was carried out in a CCl4 excess at an equimolar ratio of reagents, triethylamine was used as an HCl acceptor. The highest yields of dialkyl-N-(1-ethynylcyclohexan-1-yl)amidophosphates were achieved by adding equimolar amounts of dialkyl phosphites to the mixture of 1-ethynyl-1-aminocyclohexane, triethylamine, and CCl4 followed by the subsequent activation of the mixture in a microwave reactor (MAS-II Plus MW) (MW 102 W, 115 °C, microwave irradiation time was 3‒5 min). The composition and structure of the obtained compounds were proved by elemental analysis, IR,1 H,13 C,31 P NMR spectroscopy, and X-ray diffraction analysis (XRD). The biological tests carried out in laboratory and field conditions allowed identifying diethyl-N-(1-ethynylcyclohexan-1-yl) amidophosphate among the synthesized compounds, which produces a high growth-regulating effect on the growth, development, and yield of agricultural crops.
1-ethynyl-1-aminocyclohexane , Atherton-Todd reaction , Dialkyl phosphorous acids , Microwave irradiation
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Kazakh National Women’s Teacher Training University, 99, Aiteke bi str, Almaty, Kazakhstan
A.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8, Akad. Arbuzov str, Tatarstan Republic, Kazan, Russian Federation
Korkyt Ata Kyzylorda University, 29A, Aiteke bi str, Kyzylorda, Kazakhstan
Kazakh National Women’s Teacher Training University
A.E. Arbuzov Institute of Organic and Physical Chemistry
Korkyt Ata Kyzylorda University
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