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. 2021 Apr 12;11(22):13292-13296.
doi: 10.1039/d0ra10451e. eCollection 2021 Apr 7.

Cascade synthesis of 2,4-disulfonylpyrroles by the sulfonylation/[2 + 3]-cycloaddition reactions of gem-dibromoalkenes with arylsulfonyl methyl isocyanides

Parvin Salehi  1 , Zahra Tanbakouchian  1 , Noushin Farajinia-Lehi  1 , Morteza Shiri  1
Affiliations

Cascade synthesis of 2,4-disulfonylpyrroles by the sulfonylation/[2 + 3]-cycloaddition reactions of gem-dibromoalkenes with arylsulfonyl methyl isocyanides

Parvin Salehi et al. RSC Adv. .

Abstract

An efficient cascade reaction involving sulfonylation and [2 + 3]-cycloaddition reactions of gem-dibromoalkenes with arylsulfonyl methyl isocyanides was described for the synthesis of 3-aryl-2,4-disulfonyl-1H-pyrroles. The main highlight of this study is the introduction of a new dual-functional reactivity of arylsulfonyl methyl isocyanides as the sulfonyl source as well as a 1,3-dipolar reagent in the same reaction. This system is facilitated by Cs2CO3 mediation in DMSO and 100 °C conditions.

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Conflict of interest statement

There are no conflict to declare.

Figures

Fig. 1
Fig. 1. Structure of TosMIC.
Scheme 1
Scheme 1. ASMIC as a dual-functional reactive starting material in the same reaction.
Scheme 2
Scheme 2. Formation of 2,4-ditosyl-1H-pyrrole instead of 4-bromo-2-tosyl-1H-pyrrole.
Scheme 3
Scheme 3. A designed sequences of control experiments for mechanistic investigation.
Scheme 4
Scheme 4. A plausible reaction mechanism.
See this image and copyright information in PMC

References

    1. Estevez V. Villacampa M. Menendez J. C. Multicomponent reactions for the synthesis of pyrroles. Chem. Soc. Rev. 2010;39:4402. doi: 10.1039/B917644F. - DOI - PubMed
    2. Joshi S. D. More U. A. Kulkarni V. H. Aminabhavi T. M. Pyrrole: chemical synthesis, microwave assisted synthesis, reactions and applications: a review. Curr. Org. Chem. 2013;17:2279. doi: 10.2174/13852728113179990040. - DOI
    3. Gupton J. T., Pyrrole natural products with antitumor properties, in Heterocyclic Antitumor Antibiotics, Springer, 2006, pp. 53–92
    4. Gholap S. S. Pyrrole: an emerging scaffold for construction of valuable therapeutic agents. Eur. J. Med. Chem. 2016;110:13. doi: 10.1016/j.ejmech.2015.12.017. - DOI - PubMed
    5. Bhardwaj V. Gumber D. Abbot V. Dhiman S. Sharma P. Pyrrole: a resourceful small molecule in key medicinal hetero-aromatics. RSC Adv. 2015;5:15233. doi: 10.1039/C4RA15710A. - DOI
    6. Ahmad S. Alam O. Naim M. J. Shaquiquzzaman M. Alam M. M. Iqbal M. Pyrrole: an insight into recent pharmacological advances with structure activity relationship. Eur. J. Med. Chem. 2018;157:527. doi: 10.1016/j.ejmech.2018.08.002. - DOI - PubMed
    1. Iwao M. Fukuda T. Ishibashi F. Synthesis and biological activity of lamellarin alkaloids: an overview. Heterocycles. 2011;83:491. doi: 10.3987/REV-10-686. - DOI - PubMed
    1. Estévez V. Villacampa M. Menéndez J. C. Recent advances in the synthesis of pyrroles by multicomponent reactions. Chem. Soc. Rev. 2014;43:4633. doi: 10.1039/C3CS60015G. - DOI - PubMed
    2. Liddell J. R. Pyrrolizidine alkaloids. Nat. Prod. Rep. 2001;18:441. doi: 10.1039/B004676K. - DOI - PubMed
    3. Forte B. Malgesini B. Piutti C. Quartieri F. Scolaro A. Papeo G. The pyrrole-imidazole alkaloids. Mar. Drugs. 2009;7:705. doi: 10.3390/md7040705. - DOI - PMC - PubMed
    4. Le Quesne P. W., Dong Y. and Blythe T. A., Recent Research on Pyrrole Alkaloids, Pergamon Press, Oxford, 1999, vol. 13
    5. Ferreira V. F. de Souza M. C. B. V. Cunha A. C. Pereira L. O. R. Ferreira M. L. G. Recent advances in the synthesis of pyrroles. Org. Prep. Proced. Int. 2001;33:411. doi: 10.1080/00304940109356613. - DOI
    1. Hantzsch A. Ber. Dtsch. Chem. Ges. 1890;23:1474. doi: 10.1002/cber.189002301243. - DOI
    1. Knorr L. Synthese von pyrrolderivaten. Ber. Dtsch. Chem. Ges. 1884;17:1635. doi: 10.1002/cber.18840170220. - DOI

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