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Synthesis of novel tetra- and pentacyclic benzosultam scaffolds via domino Knoevenagel hetero-Diels–Alder reactions in water

Journal of the Iranian Chemical Society volume 10, pages 1057–1065 (2013)Cite this article

Abstract

An efficient catalyst-free and diastereoselective synthesis of novel dihydropyrano[2,3-d]pyrimidine and dihydropyrano[3,2-c]chromen-annulated benzosultams is described. A number of (E)-N-(2-formylphenyl)-N-methyl-2-phenylethenesulfonamides were synthesized and underwent a one-pot domino Knoevenagel hetero-Diels–Alder reaction, respectively, with N,N-dimethylbarbituric acid and 4-hydroxycoumarin in water, giving the desired products, in moderate to excellent yields.

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Acknowledgments

The authors acknowledge the University of Tehran and Radioisotope Research Group of NSTRI for financial support of this research.

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Authors and Affiliations

  1. School of Chemistry, College of Science, University of Tehran, P.O. Box 14155 6455, Tehran, Iran

    Mehdi Ghandi & Masoud Sadeghzadeh

  2. Radioisotope Research Group, NSTRI, P.O. Box 11365 3486, Tehran, Iran

    Shahab Sheibani, Masoud Sadeghzadeh & Fariba Johari Daha

  3. Faculty of Chemistry, Adam Mickiewicz University in Poznan, Umultowska 89b, 61-614, Poznan, Poland

    Maciej Kubicki

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  1. Mehdi Ghandi
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  2. Shahab Sheibani
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  3. Masoud Sadeghzadeh
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  4. Fariba Johari Daha
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  5. Maciej Kubicki
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Correspondence to Mehdi Ghandi.

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Ghandi, M., Sheibani, S., Sadeghzadeh, M. et al. Synthesis of novel tetra- and pentacyclic benzosultam scaffolds via domino Knoevenagel hetero-Diels–Alder reactions in water. J IRAN CHEM SOC 10, 1057–1065 (2013). https://doi.org/10.1007/s13738-013-0247-z

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