Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2024 Aug 15;14(1):18924.
doi: 10.1038/s41598-024-69817-2.

A potential DES catalyst for the fast and green synthesis of benzochromenopyrimidines and pyranopyrimidines

Arezo Monem  1 , Davood Habibi  2 , Hadis Goudarzi  1
Affiliations

A potential DES catalyst for the fast and green synthesis of benzochromenopyrimidines and pyranopyrimidines

Arezo Monem et al. Sci Rep. .

Abstract

A gentisic acid based-Deep Eutectic Solvent (MTPPBr/GA-DES) was synthesized by mixing one mole of methyl triphenylphosphonium bromide (MTPPBr) and one mole of gentisic acid (GA: 2,5-dihydroxy-benzoic acid) based on the eutectic point phase diagram. Then, it was characterized by FT-IR, NMR, densitometer, and TGA/DTA techniques and used as a potent and novel catalyst for the fast and green synthesis of: (i) Five new 2(a-e) and five known 2(f-j) benzo[6,7]chromeno[2,3-d]pyrimidines and (ii) One new (3a) and eleven known 3(b-l) pyrano[2,3-d]pyrimidines, in solvent-free conditions, short reaction times, and high yields. It is important to mention that for the synthesis of 2(a-j), there is only one reference which states that the reaction times are extremely long (720-2400 min), while these times are reduced to approximately 35-50 min in our proposed strategy, indicatinging that the rate of reactions will be 20-48 times faster, which is the clear and most obvious advantage of our approach.

Keywords: Deep eutectic solvent; Gentisic acid; Green synthesis; benzo[6,7]chromeno[2,3-d]pyrimidines; pyrano[2,3-d]pyrimidines.

PubMed Disclaimer

Conflict of interest statement

The authors declare no competing interests.

Figures

Figure 1
Figure 1
Preparation of the DES catalyst.
Figure 2
Figure 2
Synthesis of 2(a-j) and 3(a-l) by DES.
Figure 3
Figure 3
The FT-IR spectra of (a), (b), (c), and (d).
Figure 4
Figure 4
The 1H NMR of MTPPBr.
Figure 5
Figure 5
The 1H NMR spectrum of GA.
Figure 6
Figure 6
The 1H NMR of the DES catalyst.
Figure 7
Figure 7
The TGA-DTA pattern.
Figure 8
Figure 8
The eutectic points phase diagram.
Figure 9
Figure 9
Proposed mechanism for the synthesis of 2(a-j).
Figure 10
Figure 10
Reusability of DES.
Figure 11
Figure 11
Proposed mechanism for the synthesis of 3(a-l).
Figure 12
Figure 12
Reusability of DES.
See this image and copyright information in PMC

References

    1. Abbott, A. P. et al. Preparation of novel, moisture-stable, Lewis-acidic ionic liquids containing quaternary ammonium salts with functional side chains electronic supplementary information (ESI) available: Plot of conductivity vs. temperature for the ionic liquid. Chem. Commun.1, 2010–2011 (2001).10.1039/b106357j - DOI - PubMed
    1. Abbott, A. P., Boothby, D., Capper, G., Davies, D. L. & Rasheed, R. K. Deep eutectic solvents formed between choline chloride and carboxylic acids: Versatile alternatives to ionic liquids. J. Am. Chem. Soc.126, 9142–9147 (2004). 10.1021/ja048266j - DOI - PubMed
    1. Abbott, A. P., Capper, G., Davies, D. L., Rasheed, R. K. & Tambyrajah, V. Novel solvent properties of choline chloride/urea mixtures. Chem. Commun.1, 70–71 (2003).10.1039/b210714g - DOI - PubMed
    1. Walden, P. Molecular weights and electrical conductivity of several fused salts. Bulletin Acad. Imper. Sci.1800, 405–422 (1914).
    1. Paiva, A. et al. Natural deep eutectic solvents–solvents for the 21st century. ACS Sustain. Chem. Eng.2, 1063–1071 (2014).10.1021/sc500096j - DOI

LinkOut - more resources