Skip to main content

Advertisement

SpringerLink
Log in

Water extract of red mud: an efficient and renewable medium for environmentally benign synthesis of 2-amino-4H-chromenes

  • Short Communication
  • Published:
Molecular Diversity Aims and scope Submit manuscript

Abstract

In this study, an efficient and convenient domino Michael addition/intramolecular cyclization protocol is presented for the synthesis of biologically relevant 2-amino-4H-chromenes in short reaction times using water extract of red mud (WERM) at room temperature. Red mud is generated abundantly as wastes in aluminum industries and this is the first report to utilize WERM as an effective and renewable medium in organic synthesis. As the precursor material is a waste, the present method is environmentally benign and economical. The final 2-amino-4H-chromenes were obtained in high yields by simple precipitation and subsequent washing by aqueous ethanol which eliminates the chromatographic separation. The present method is tolerated by electronically diverse functional groups and also applicable for large-scale synthesis. Moreover, WERM was recovered from the reaction medium and reused for several cycles without significant loss of reactivity.

Graphical abstract

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Fig. 2
Scheme 2
Fig. 3

References

  1. Elinson MN, Dorofeev AS, Miloserdov FM, Ilovaisky AI, Feducovich SK, Belyakov PA, Nikishin GI (2008) Catalysis of salicylaldehydes and two different C-H acids with electricity: first example of an efficient multicomponent approach to the design of functionalized medicinally privileged 2-amino-4H-chromene scaffold. Adv Synth Catal 350:591–601

    Article  CAS  Google Scholar 

  2. Kidwai M, Saxena S, Khan MK, Thukral SS (2005) Aqua mediated synthesis of substituted 2-amino-4H-chromenes and in vitro study as antibacterial agents. Bioorg Med Chem Lett 15(19):4295–4298

    Article  CAS  Google Scholar 

  3. Hiremath PB, Kamanna K (2019) A microwave accelerated sustainable approach for the synthesis of 2-amino-4H-chromenes catalysed by WEPPA: a green strategy. Curr Microw Chem 6:30–43

    Article  CAS  Google Scholar 

  4. Ellis GP (1977) Chromenes, chromanones, and chromones. In: Weissberger A, Taylor EC (eds) The chemistry of heterocyclic compounds. Chromenes, Chromanes and Chromeones, chapter 2. Wiley, New York, pp 11–139

    Chapter  Google Scholar 

  5. Hafez EAA, Elnagdi MH, Elagamey AGA, El-Taweel FMAA (1987) Nitriles in heterocyclic synthesis: novel synthesis of benzo[c]coumarin and of benzo[c]pyrano[3,2-c]quinoline derivatives. Heterocycles 26(4):903–907

    Article  CAS  Google Scholar 

  6. Tashrifi Z, Mohammadi-Khanaposhtani M, Hamedifar H, Larijani B, Ansari S, Mahdavi M (2020) Synthesis and pharmacological properties of polysubstituted 2-amino-4H-pyran-3-carbonitrile derivatives. Mol Divers 24:1385–1431

    Article  CAS  Google Scholar 

  7. Mamaghania M, Nia RH, Tavakoli F, Jahanshahi P (2018) Recent advances in the MCRs synthesis of chromenes: a review. Curr Org Chem 22:1704–1769

    Article  Google Scholar 

  8. Heravi MM, Zadsirjan V, Mollaiye M, Heydari M, Koshvandi ATK (2018) Salicylaldehydes as privileged synthons in multicomponent reactions. Russ Chem Rev 87:553–585

    Article  CAS  Google Scholar 

  9. Das D (2021) Ascorbic acid: an efficient organocatalyst for environmentally benign synthesis of indole-substituted 4H-chromenes. Monatshefte für Chem-Chem Mon 152:987–991

    Article  CAS  Google Scholar 

  10. Zheng Y-Q, Luan C-F, Wang Z-J, Yao Y-Q, Shi Z-C, Li X-F, Zhao Z-G, Chen F (2016) Enantioselective synthesis of 2-amino-3-nitrile-chromenes catalyzed by cinchona alkaloids: a remarkable additive effect. Chin Chem Lett 27:25–30

    Article  CAS  Google Scholar 

  11. Xie J-W, Huang X, Fan L-P, Xu D-C, Li X-S, Su H, Wena Y-H (2009) Efficient method for the synthesis of optically active 2-amino-2-chromene derivatives via one-pot tandem reactions. Adv Synth Catal 351:3077–3082

    Article  CAS  Google Scholar 

  12. Li L-Y, Zeng Q-Q, Yang Y-X, Hu H-F, Xu M, Guan Z, He Y-H (2015) A domino reaction for the synthesis of 2-amino-4H-chromene derivatives using bovine serum albumin as a catalyst. J Mol Catal B Enzym 122:1–7

    Article  CAS  Google Scholar 

  13. Yin G, Shi H, Xu L, Wei X, Tao Q (2013) Selective synthesis of cyano-functionalized 2-aryl-4H-chromenes and 2-amino-4H-chromene-3-carbonitriles by catalyst-tuned reactions of 2-hydroxychalcones with 2-substituted acetonitriles. Synthesis 45:0334–0340

    Article  CAS  Google Scholar 

  14. Pontes O, Costa M, Santos F, Sampaio-Marques B, Dias T, Ludovico P, Baltazar F, Proença F (2018) Exploitation of new chalcones and 4H-chromenes as agents for cancer treatment. Eur J Med Chem 157:101–114

    Article  CAS  Google Scholar 

  15. Balakrishnan M, Batra VS, Hargreaves JSJ, Pulford ID (2011) Waste materials–catalytic opportunities: an overview of the application of large scale waste materials as resources for catalytic applications. Green Chem 13:16–24

    Article  CAS  Google Scholar 

  16. Sarmah M, Mondal M, Utpal B (2017) Agro-waste extract based solvents: emergence of novel green solvent for the design of sustainable processes in catalysis and organic chemistry. ChemistrySelect 2:5180–5188

    Article  CAS  Google Scholar 

  17. Chia PW, Lim BS, Yong FSJ, Poh S-C, Kan S-Y (2018) An efficient synthesis of bisenols in water extract of waste onion peel ash. Environ Chem Lett 16:1493–1499

    Article  CAS  Google Scholar 

  18. Sun Y, Jin W, Liu C (2019) Trash to treasure: eco-friendly and practical synthesis of amides by nitriles hydrolysis in WEPPA. Molecules 24:3838

    Article  CAS  Google Scholar 

  19. Godoi M, Leitemberger A, Böhs LMC, Silveira MV, Rafique J, D’Oca MGM (2019) Rice straw ash extract, an efficient solvent for regioselective hydrothiolation of alkynes. Environ Chem Lett 17:1441–1446

    Article  CAS  Google Scholar 

  20. Mishra S, Bal R, Dey RK (2021) Heterogeneous recyclable copper oxide supported on activated red mud as an efficient and stable catalyst for the one pot hydroxylation of benzene to phenol. Mol Catal 499:111310

    Article  CAS  Google Scholar 

  21. Yang G, Luo C, Mu X, Wang T, Liu X-Y (2012) Highly efficient enantioselective three component synthesis of 2-amino-4H-chromenes catalysed by chiral tertiary amine-thioureas. Chem Commun 48:5880–5882

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors gratefully acknowledge the financial support from Science & Engineering Research Board (Grant YSS/2015/001425 & ECR/2017/000378) and UGC [F.4-5(207-FRP)/2015(BSR)].

Author information

Authors and Affiliations

  1. Department of Chemistry, Central University of Jharkhand, Ranchi, Jharkhand, India

    Snigdha Rani Patra & Sabyasachi Bhunia

  2. Department of Chemistry, Triveni Devi Bhalotia College, Raniganj, India

    Debjit Das

Authors
  1. Snigdha Rani Patra
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sabyasachi Bhunia
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Debjit Das
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Sabyasachi Bhunia or Debjit Das.

Ethics declarations

Conflict of interest

The author states that there is no conflict of interest.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (PDF 3515 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Patra, S.R., Bhunia, S. & Das, D. Water extract of red mud: an efficient and renewable medium for environmentally benign synthesis of 2-amino-4H-chromenes. Mol Divers 26, 2907–2914 (2022). https://doi.org/10.1007/s11030-021-10369-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11030-021-10369-2

Keywords

Search

Navigation