Three-Component Reaction of 3-Formyl-6-Methylchromone, Primary Amines, and Secondary Phosphine Oxides: A Synthetic and Mechanistic Study.

A fast, mild, and efficient catalyst-free approach has been developed for the synthesis of chromonyl-substituted α-aminophosphine oxides by the three-component reaction of 3-formyl-6-methylchromone, primary amines, and secondary phosphine oxides at ambient temperature. Carrying out the reaction with aliphatic amines or aminoalcohols at a higher temperature (80 °C), phosphinoyl-functionalized 3-aminomethylene chromanones were formed instead of the corresponding chromonyl-substituted α-aminophosphine oxides. No reaction occurred when 3-formyl-6-methylchromone and secondary phosphine oxides were reacted with aromatic amines in the absence of any catalyst.

Multicomponent Synthesis of Potentially Biologically Active Heterocycles Containing a Phosphonate or a Phosphine Oxide Moiety.

Several multicomponent synthetic approaches were elaborated for plenty of novel nitrogen or oxygen heterocycles containing a phosphonate or a phosphine oxide moiety. All multicomponent reactions were optimized through a model reaction in respect of the heating mode, molar ratio of the starting materials, atmosphere, catalyst, temperature, reaction time and solvent applied, and then, the extended preparation of small libraries of structurally-related compounds was performed. Most of the reactions could be considered as "green syntheses", as they were carried out in the absence of any catalyst and/or solvent using microwave (MW) irradiation or even at ambient temperature.

Study of the Three-Component Reactions of 2-Alkynylbenzaldehydes, Aniline, and Dialkyl Phosphites-The Significance of the Catalyst System.

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.

Three-component synthesis, utilization and biological activity of phosphinoyl-functionalized isoindolinones.

A new method for the synthesis of 3-oxoisoindolin-1-ylphosphine oxides bearing same or different substituents on the phosphorus atom is described. The one-pot three-component reaction of 2-formylbenzoic acid, primary amines and achiral or P-stereogenic secondary phosphine oxides provided the target compounds under catalyst-free, mild conditions and for short reaction times. The deoxygenation of a 3-oxoisoindolin-1-ylphosphine oxide was also studied, and the phosphine obtained could be converted to a sulphide and to a platinum complex.

PMDTA-catalyzed multicomponent synthesis and biological activity of 2-amino-4H-chromenes containing a phosphonate or phosphine oxide moiety.

A new approach for the preparation of (2-amino-3-cyano-4H-chromen-4-yl)phosphonate derivatives is described. The multicomponent reaction of salicylaldehydes, malononitrile and dialkyl phosphites catalyzed by pentamethyldiethylenetriamine (PMDTA) provided the bicyclic derivatives in high yields. The method developed did not require chromatographic separation, since the products could be recovered from the reaction mixture by simple filtration.