Synthesis of isoindolinone phosphonates and their related derivatives by multicomponent reaction

Abstract

An efficient catalyst-free microwave (MW)-assisted method was elaborated for the batch and continuous flow synthesis of N-alkyl-isoindolinone phosphonates by the three-component reaction of 2-formylbenzoic acid, primary amines and various dialkyl phosphites. The reaction was also extended to various secondary phosphine oxides and primary amines, as well. In order to obtain more information about the condensation, the reaction mechanism was also studied by in situ FT-IR spectroscopy.

Graphical Abstract

Keywords:

• N-heterocycles
• isoindolinone phosphonates
• isoindolinone phosphine oxides
• Kabachnik-Fields reaction
• continuous flow reactor
• in situ FT-IR spectroscopy

Acknowledgement

The authors thank to Avidin Ltd. for the biological activity investigations.

Additional information

Funding

The project was supported by the Hungarian Research Development and Innovation Office (FK123961), by the National Research, Development and Innovation Fund of Hungary in the frame of the FIEK_16-1-2016-0007 (Higher Education and Industrial Cooperation Center) project, B.R. was supported by the ÚNKP-19-1-I-BME-165 New National Excellence Program of the Ministry for Innovation and Technology. N. P.-T. was supported by the Servier-Beregi PhD Research Fellowship, E.B. was supported by the János Bolyai Research Scholarship of the Hungarian Academy of Sciences (BO/00278/17/7).