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Molecules
Volume 25
Issue 14
10.3390/molecules25143307
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Article

Study on the Microwave-Assisted Batch and Continuous Flow Synthesis of N-Alkyl-Isoindolin-1-One-3-Phosphonates by a Special Kabachnik–Fields Condensation

by
Ádám Tajti
1,
Nóra Tóth
1,
Bettina Rávai
1,
István Csontos
1,
Pál Tamás Szabó
2 and
Erika Bálint
1,*
1
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary
2
MS Metabolomics Laboratory, Instrumentation Center, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok krt. 2., H-1117 Budapest, Hungary
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Molecules 2020, 25(14), 3307; https://doi.org/10.3390/molecules25143307
Received: 30 June 2020 / Revised: 16 July 2020 / Accepted: 17 July 2020 / Published: 21 July 2020
(This article belongs to the Special Issue Recent Developments in the Synthesis and Utilization of Organophosphorus Compounds)
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Abstract

A simple and efficient microwave (MW)-assisted method was elaborated for the catalyst-free synthesis of isoindolin-1-one-3-phosphonates by the three-component condensation of 2-formylbenzoic acid, aliphatic primary amines and various dialkyl phosphites. The batch and the continuous flow reactions were optimized in respect of the temperature, the reaction time and the molar ratio of the starting materials. To evaluate the potential of MW irradiation, comparative thermal experiments were also carried out. In order to obtain “real time” information about the condensation, the special Kabachnik–Fields reaction of 2-formylbenzoic acid, butylamine and diethyl phosphite was monitored by in situ FT-IR spectroscopy. The novel title compounds could be prepared in high yields at low temperature under a short reaction time. A suitable method could also be developed for the preparation of the isoindolin-1-one-3-phosphonates at a “few g” scale by using a continuous flow MW reactor. View Full-Text
Keywords: isoindolin-1-one phosphonates; α-aminophosphonate derivatives; three-component condensation; Kabachnik–Fields reaction; microwave; in situ FT-IR spectroscopy; continuous flow microwave reactor isoindolin-1-one phosphonates; α-aminophosphonate derivatives; three-component condensation; Kabachnik–Fields reaction; microwave; in situ FT-IR spectroscopy; continuous flow microwave reactor
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited

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MDPI and ACS Style

Tajti, Á.; Tóth, N.; Rávai, B.; Csontos, I.; Szabó, P.T.; Bálint, E. Study on the Microwave-Assisted Batch and Continuous Flow Synthesis of N-Alkyl-Isoindolin-1-One-3-Phosphonates by a Special Kabachnik–Fields Condensation. Molecules 2020, 25, 3307. https://doi.org/10.3390/molecules25143307

AMA Style

Tajti Á, Tóth N, Rávai B, Csontos I, Szabó PT, Bálint E. Study on the Microwave-Assisted Batch and Continuous Flow Synthesis of N-Alkyl-Isoindolin-1-One-3-Phosphonates by a Special Kabachnik–Fields Condensation. Molecules. 2020; 25(14):3307. https://doi.org/10.3390/molecules25143307

Chicago/Turabian Style

Tajti, Ádám, Nóra Tóth, Bettina Rávai, István Csontos, Pál T. Szabó, and Erika Bálint. 2020. "Study on the Microwave-Assisted Batch and Continuous Flow Synthesis of N-Alkyl-Isoindolin-1-One-3-Phosphonates by a Special Kabachnik–Fields Condensation" Molecules 25, no. 14: 3307. https://doi.org/10.3390/molecules25143307

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