Skip to main content
Log in

Lactic Acid as a Highly Efficient and Simplified Biocatalyst System for One-Step Synthesis of Multisubstituted Pyrroles

  • Research paper
  • Published:
Iranian Journal of Science and Technology, Transactions A: Science Aims and scope Submit manuscript

Abstract

An acid-mediated three-component reaction for the synthesis of multisubstituted pyrroles has been developed from benzoin, C–H-activated compounds, and ammonium acetate/p-methoxy aniline. The advantage of this one-step metal-free approach is the use of lactic acid as a biodegradable, environmentally benign, and available catalyst and green solvent along with simple purification process involving no chromatographic process, high efficiency, short reaction time, and high yield of products.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Scheme 2

Similar content being viewed by others

References

  • Anastas PT, Warner JC (2000) Green chemistry: theory and practice, vol 30. Oxford University Press, Oxford

    Google Scholar 

  • Arthur CR, Gupton JT, Kellogg GE, Yeudall WA, Cabot MC, Newsham IF, Gewirtz DA (2007) Autophagic cell death, polyploidy and senescence induced in breast tumor cells by the substituted pyrrole JG-03-14, a novel microtubule poison. Biochem Pharmacol 74:981–991

    Article  Google Scholar 

  • Bhat SI, Trivedi DR (2013) A catalyst-and solvent-free three-component reaction for the regioselective one-pot access to polyfunctionalized pyrroles. Tetrahedron Lett 54:5577–5582

    Article  Google Scholar 

  • Brandish PE, Sparey T, Campbell A, Pike A, Brandon N, Zheng W (2009) Use of fused pyrrole carboxylic acids for the treatment of neurodegenerative and psychiatric diseases and d-amino acid oxidase inhibitors. US patent application 11/992,913

  • Burkholder PR, Pfister RM, Leitz FH (1996) Production of a pyrrole antibiotic by a marine bacterium. Appl Microbiol 14:649–653

    Google Scholar 

  • Clive DL, Cheng P, Peng H, Dornevil KH, Draganov AB, Chen W, Dai C, Nelson WH, Liu A, Wang B (2013) The marinopyrroles. Tetrahedron 69:5059–5066

    Article  Google Scholar 

  • Dolzhenko AV, Dolzhenko AV (2015) Green solvents for eco-friendly synthesis of bioactive heterocyclic compounds. In: Brahmachari G (ed) Green synthetic approaches for biologically relevant heterocycles. Elsevier, Amsterdam, pp 101–139

    Chapter  Google Scholar 

  • Farahi M, Davoodi M, Tahmasebi M (2016) A new protocol for one-pot synthesis of tetrasubstituted pyrroles using tungstate sulfuric acid as a reusable solid catalyst. Tetrahedron Lett 57:1582–1584

    Article  Google Scholar 

  • Fatahpour M, Hazeri N, Maghsoodlou MT, Lashkari M (2017a) One-pot condensation approach for synthesis of diverse naphthopyranopyrimidines utilizing lactic acid as efficient and eco-friendly catalyst. Polycycl Aromat Compd 2017:1–7

    Google Scholar 

  • Fatahpour M, Hazeri N, Maghsoodlou MT, Lashkari M (2017b) A green approach for the one-pot, three-component synthesis of 2-arylpyrroloacridin-1 (2H)-ones using lactic acid as a bio-based catalyst under solvent-free conditions. J Chin Chem Soc 64:1071–1078

    Article  Google Scholar 

  • Fatahpour M, Hazeri N, Maghsoodlou MT, Lashkari M (2018a) Metal-free greener method for the synthesis of densely functionalized pyrroles via a one-pot three-component reaction. J Iran Chem Soc. https://doi.org/10.1007/s13738-018-1486-9

    Google Scholar 

  • Fatahpour M, Hazeri N, Maghsoodlou MT, Lashkari M, Lactic Acid (2018b) A new application as an efficient catalyst for the green one-pot synthesis of 2-hydroxy-12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-one and 12-aryl-8,9,10,12-tetrahydrobenzo[a] xanthen-11-one analogs. Iran J Sci Technol Trans A Sci 42:533–538

    Article  Google Scholar 

  • Ganem B (2009) Strategies for innovation in multicomponent reaction design. Acc Chem Res 42:463–472

    Article  Google Scholar 

  • Ghabraie E, Balalaie S, Bararjanian M, Bijanzadeh HR, Rominger F (2011) An efficient one-pot synthesis of tetra-substituted pyrroles. Tetrahedron 67:5415–5420

    Article  Google Scholar 

  • Harrak Y, Rosell G, Daidone G, Plescia S, Schillaci D, Pujol M (2007) Synthesis and biological activity of new anti-inflammatory compounds containing the 1,4-benzodioxine and/or pyrrole system. Bioorg Med Chem 15:4876–4890

    Article  Google Scholar 

  • Hildebrandt A, Schaarschmidt D, Lang H (2011) Electronically intercommunicating iron centers in di-and tetraferrocenyl pyrroles. Organometallics 2011:556–563

    Article  Google Scholar 

  • Iwao M, Fukuda T, Ishibashi F (2011) Synthesis and biological activity of lamellarin alkaloids: an overview. Heterocycles 83:491–529

    Article  Google Scholar 

  • Joshi S, Vagdevi H, Vaidya V, Gadaginamath G (2008) Synthesis of new 4-pyrrol-1-yl benzoic acid hydrazide analogs and some derived oxadiazole, triazole and pyrrole ring systems: a novel class of potential antibacterial and antitubercular agents. Eur J Med Chem 43:1989–1996

    Article  Google Scholar 

  • Kangani M, Hazeri N, Maghsoodlou MT (2017a) Synthesis of pyrrole and furan derivatives in the presence of lactic acid as a catalyst. J Saudi Chem Soc 21:160–164

    Article  Google Scholar 

  • Kangani M, Hazeri N, Yazdani-Elah-Abadi A, Maghsoodlou MT (2017b) Lactic acid: an efficient and green catalyst for the one-pot five-components synthesis of highly substituted piperidines. Polycycl Aromat Compd. https://doi.org/10.1080/10406638.2016.1207686

    Google Scholar 

  • Kunfermann A, Witschel M, Illarionov B, Martin R, Rottmann M, Höffken HW, Seet M, Eisenreich W, Knölker HJ, Fischer M (2014) Pseudilins: halogenated, allosteric inhibitors of the non-mevalonate pathway enzyme IspD. Angew Chem Int Ed 53:2235–2239

    Article  Google Scholar 

  • Ruijter E, Scheffelaar R, Orru RV (2011) Multicomponent reaction design in the quest for molecular complexity and diversity. Angew Chem Int Ed 50:6234–6246

    Article  Google Scholar 

  • Sheldon R (2017) The E-factor 25 years on: the rise of green chemistry and sustainability. Green Chem 19:18–43

    Article  Google Scholar 

  • Tamaddon F, Alizadeh M (2015) Cocamidopropyl betaine catalyzed benzoin condensation and pseudo-four-component reaction of the in situ formed benzoin in water. Synlett 26:525–530

    Article  Google Scholar 

  • Tamaddon F, Farahi M, Karami B (2012) Molybdate sulfuric acid as a reusable solid catalyst in the synthesis of 2,3,4,5-tetrasubstituted pyrroles via a new one-pot [2 + 2 + 1] strategy. J Mol Catal A Chem 356:85–89

    Article  Google Scholar 

  • Tamuly C, Dutta PP, Bordoloi M, Bora J (2013) Antifungal and antioxidant pyrrole derivative from Piper pedicellatum. Nat Prod Commun 8:1451–1454

    Google Scholar 

  • Wang SF, Guo CL, Cui KK, Zhu YT, Ding JX, Zou XY, Li YH (2015) Lactic acid as an invaluable green solvent for ultrasound-assisted scalable synthesis of pyrrole derivatives. Ultrason Sonochem 26:81–86

    Article  Google Scholar 

Download references

Acknowledgements

We gratefully appreciate the financial support from the Research Council of University of Sistan and Baluchestan.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Nourallah Hazeri.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sanchooli Tazeh, K., Hazeri, N., Fatahpour, M. et al. Lactic Acid as a Highly Efficient and Simplified Biocatalyst System for One-Step Synthesis of Multisubstituted Pyrroles. Iran J Sci Technol Trans Sci 43, 2213–2218 (2019). https://doi.org/10.1007/s40995-018-0657-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s40995-018-0657-y

Keywords

Navigation