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Two stereoisomers of butenedioic acid-mediated synthesis of tetrahydropyridine carboxylate derivatives with the same stereochemistry

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Abstract

Fumaric and maleic acids are utilized as two environmental-friendly and efficient catalysts for a one-pot, pseudo five-component coupling reaction, containing aromatic amines, aromatic aldehydes and methyl acetoacetate/ethyl acetoacetate. In this work, a variety of differently substituted aldehydes and amines were tolerated very well, affording cyclic compounds with two consecutive stereogenic centers in moderate to high yields and with excellent diastereoselectivities. In this research, the catalytic effect of maleic acid is compared with that of fumaric acid. According to the obtained results in the presence of both of them, products were produced with the same streochemistry. These reactions were performed under mild conditions to yield 1,2,5,6-tetrahydropyridine-3-carboxylate derivatives with good to excellent yields (46–91%). When fumaric acid was used instead of maleic acid as catalyst the yields of products were relatively low. This is probably because of the stereochemistry of fumaric acid. The main benefits of this process are the easy work-up, short reaction times, green catalysts and no chromatographic purifications. The work-up of these reactions involves only a filtration and a simple washing step with EtOH, and there is no need for column chromatography.

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Acknowledgments

The University of Sistan and Baluchestan is thanked for supporting this work.

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Authors and Affiliations

  1. Young Researchers and Elites Club, Science and Research Branch, Islamic Azad University, Tehran, Iran

    Seyyed Rasul Mousavi

  2. Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, Zahedan, P.O. Box 98135-674, Iran

    Malek Taher Maghsoodlou & Ali Roygar

  3. Faculty of Science, Velayat University, Iranshahr, Iran

    Mojtaba Lashkari

Authors
  1. Seyyed Rasul Mousavi
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  2. Malek Taher Maghsoodlou
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  3. Ali Roygar
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  4. Mojtaba Lashkari
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Correspondence to Malek Taher Maghsoodlou.

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Mousavi, S.R., Maghsoodlou, M.T., Roygar, A. et al. Two stereoisomers of butenedioic acid-mediated synthesis of tetrahydropyridine carboxylate derivatives with the same stereochemistry. Res Chem Intermed 44, 675–690 (2018). https://doi.org/10.1007/s11164-017-3127-9

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  • DOI: https://doi.org/10.1007/s11164-017-3127-9

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