New biologically active phosphonium salts based on 3-(diphenylphosphino)propionic acid and unsaturated amides
- PDF / 802,911 Bytes
- 4 Pages / 612 x 792 pts (letter) Page_size
- 83 Downloads / 155 Views
1569
New biologically active phosphonium salts based on 3-(diphenylphosphino)propionic acid and unsaturated amides* Yu. V. Bakhtiyarova,a M. V. Morozov,a S. R. Romanov,a R. R. Minnullin,a M. P. Shulaeva,b O. K. Pozdeev,b I. V. Galkina,a and V. I. Galkina aKazan
(Volga region) Federal University, 18 ul. Kremlevskaya, 420008 Kazan, Russian Federation. E-mail: [email protected] bKazan State Medical Academy, 11 ul. Mushtari, 420012 Kazan, Russian Federation New carboxylate phosphabetaines were synthesized from 3-(diphenylphosphino)propionic acid and unsaturated amides. Alkylation of the synthesized carboxylate phosphabetaines with haloalkyles was studied. In vitro biological activity of the synthesized phosphonium salts was evaluated. Keywords: carboxylate phosphabetaine, phosphonium salt, 3-(diphenylphosphino)propionic acid, acrylamide.
Carboxylate phosphabetaines and their derivatives are a wide family of organophosphorus compounds. They mimic natural amino acids and possess different valuable properties. Some phosphabetaines can be used in organic synthesis as bifunctional catalysts1 and difluoromethylating agents.2 Phosphonium salts can serve as the starting material for the synthesis of ionic liquids3—6 and biologically active substances.7—9 Therefore, the studies on the synthesis, structure, and properties of carboxylate phosphabetaines are a great challenge in modern organophosphorus chemistry. Recently, we have developed two methods for synthesizing carboxylate phosphabetaines that employed one- and two-step procedures. A one-step method is a nucleophilic addition of the tertiary phosphines to unsaturated carboxylic acids.10—15 A two-step method involves the reaction of tertiary phosphines with halocarboxylic acids and the subsequent dehydrohalogenation of the intermediates.16 We also studied alkylation of the carboxylate phosphabetaines under different conditions.17
addition of this phosphine to unsaturated amides (Scheme 1). 3-(Diphenylphosphino)propionic acid reacts with acrylamide to give compound 1 bearing the carboxylate and amide groups. The reaction of 3-(diphenylphosphino)propionic acid with 2-acrylamido-2-methylpropanesulfonic acid results in the crystalline product 2. Scheme 1
Results and Discussion In the present work, 3-(diphenylphosphino)propionic acid was used as a tertiary phosphine. Along with the tertiary phosphorus atom, this phosphine contains the carboxyl group that can play a role of an additional donor of the protons promoting quaternization of the phosphorus atom. We were interested in studying nucleophilic * Based on the materials of the International Conference "Chemistry of Organoelement Compounds and Polymers 2019" (November 18—22, 2019, Moscow, Russia).
3-(Diphenylphosphino)propionic acid reacts with unsaturated amides relatively rapidly at room temperature to provide good yields of the products. Compounds 1 and
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1569—1572, August, 2020. 1066-5285/20/6908-1569 © 2020 Springer Science+Business
Data Loading...