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1,3-(4,4'-dipyridinium disulfonic acid)propane dimethanesulfonate as an effective double-functional catalyst in preparing N,N′-Methylene bisamides, Tetrahydrochromeno-chromenes, and Pyrido-dipyrimidines

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Abstract

In this paper, a dual-functional Brønsted acidic ionic liquid (BAIL) catalyst, namely 1,3-(4,4'-dipyridinium disulfonic acid)propane dimethanesulfonate (DPDSPDM), was produced, and its structure was identified using TGA, FT-IR, 13C NMR, 1H NMR, and mass spectrometry techniques. Then, it was utilized as a versatile, homogeneous, and recyclable catalyst in preparing N,N'-Methylene bisamides (1a-14a, 5–13 min, 90–98%, 50 °C, solvent-free), Tetrahydrochromeno-chromenes (1b-12b, 8–20 min, 91–98%, 60 °C, solvent-free), and Pyrido-dipyrimidines (1c-12c, 2–5 min, 93–98%, 25 °C, H2O). In all three synthetic routes, the catalytic activity scope of DPDSPDM was remarkable and general due to having basic (MeSO3ˉ) and acidic (SO3H) sites, and reasonable mechanisms were displayed to support this high performance. The reproducibility of this homogeneous catalyst along with advantages such as appropriate TOF (turnover frequency) and TON (turnover number) values, mild conditions, simplicity of the workup, short reaction times, high yields, non-metallic nature of the catalyst, and the use of cheap and available raw materials in its synthesis; making it a potential candidate for future research.

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Acknowledgements

The authors are grateful to acknowledge the Takin Shimi Sepanta Industries Co, Ilam, Iran.

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The authors have no relevant financial or non-financial interests to disclose.

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EAMS synthesized derivatives 1a-8a and 1b-12b. BMA synthesized derivatives 9a- 14a and 1c-12c. HKM wrote the entire paper and optimized the preparation conditions of Tetrahydrochromeno-chromenes. AFK determined the structure of the ionic liquid catalyst by 1H NMR, 13CNMR. IBS identified the structure of the ionic liquid catalyst by TGA, FT-IR and mass techniques. PG identified the structure of some products through 1H NMR,13CNMR, FT-IR and mass techniques. AMH optimized the preparation conditions of N,N'-Methylene Bisamides. AA edited the entire manuscript. USA helped to edit the paper and designed the graphical abstract. MSGN synthesized the ionic liquid catalyst and optimized the preparation conditions of Pyrido-dipyrimidines.

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Correspondence to Maryam Sadat Ghorayshi Nejad.

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Saleh, E.A.M., Abdullah, B.M., Mohammed, H.K. et al. 1,3-(4,4'-dipyridinium disulfonic acid)propane dimethanesulfonate as an effective double-functional catalyst in preparing N,N′-Methylene bisamides, Tetrahydrochromeno-chromenes, and Pyrido-dipyrimidines. Res Chem Intermed 50, 3327–3349 (2024). https://doi.org/10.1007/s11164-024-05290-w

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