Skip to main content
SpringerLink
Log in

Unexpected synthesis of 4-(4,5-dihydro-1H-imidazol-2-ylsulfanyl)butyl-H-sulfite as a catalyst for the synthesis of pyrazolophthalazines

  • Original Article
  • Published:
Molecular Diversity Aims and scope Submit manuscript

Abstract

Several attempts for preparation of 4,4′-(2-thioxoimidazolidine-1,3-diyl)bis(butane-1-sulfonic acid) were not successful despite taking 2 mmol of 1,4-butane sultone in reaction with 1 mmol of imidazolidine-2-thione. Instead, 4-(4,5-dihydro-1H-imidazol-2-ylsulfanyl)butyl hydrogen sulfite (DISBHS) was prepared unexpectedly, characterized and used for the synthesis of diverse pyrazolophthalazines from the one-pot three component condensation reaction of phthalhydrazide, malononitrile and aldehydes under mild conditions.

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

Scheme 1
Scheme 2
Scheme 3
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Scheme 4
Fig. 6

Similar content being viewed by others

References

  1. Gerencser J, Dorman G, Darvas F (2006) Meldrum’s acid in multicomponent reactions: applications to combinatorial and diversity-oriented synthesis. QSAR Combust Sci 25:439–448

    Article  CAS  Google Scholar 

  2. Ramon DJ, Yus M (2005) Asymmetric multicomponent reactions (AMCRs): the new frontier. Angew Chem Int Ed 44:1602–1634

    Article  CAS  Google Scholar 

  3. Bergstrom FW (1944) Heterocyclic nitrogen compounds. Part IIA. Hexacyclic compounds: pyridine, quinoline and isoquinoline. Chem Rev 35:77–277

    Article  CAS  Google Scholar 

  4. Lichtenthaler FW (2002) Unsaturated O- and N-heterocycles from carbohydrate feedstock. Acc Chem Res 35:728–737

    Article  CAS  PubMed  Google Scholar 

  5. Orru RVA, de Greef M (2003) Recent advances in solution-phase multicomponent methodology for the synthesis of heterocyclic compounds. Synthesis 10:1471–1499

    Article  Google Scholar 

  6. Kirsch G, Hesse S, Comel A (2004) Synthesis of five- and six-membered heterocyclic through palladium catalyzed reactions. Curr Org Synth 1:47–63

    Article  CAS  Google Scholar 

  7. Scholten JD (2013) From soluble to supported iridium metal nanoparticles: active and recyclable catalysts for hydrogenation reactions. Curr Org Chem 17:348–363

    Article  CAS  Google Scholar 

  8. Watanabe N, Kabasawa Y, Takase Y, Matsukura M, Miyazaki K, Ishihara H, Kodama K, Adachi H (1998) 4-Benzylamino-1-chloro-6-substituted phthalazines: synthesis and inhibitory activity toward phosphodiesterase 5. J Med Chem 41:3367–3372

    Article  CAS  PubMed  Google Scholar 

  9. Nomoto Y, Obase H, Takai H, Teranishi M, Nakamura J, Kubo K (1990) Studies on cardiotonic agents. II: synthesis of novel phthalazine and 1,2,3-benzotriazine derivatives. Chem Pharm Bull 38:2179–2183

    Article  CAS  Google Scholar 

  10. Barbuceanu SF, Saramet G, Almajan GL, Draghici C, Barbuceanu F, Bancescu G (2012) New heterocyclic compounds from 1,2,4-triazole and 1,3,4-thiadiazole class bearing diphenylsulfone moieties. Synthesis, characterization and antimicrobial activity evaluation. Eur J Med Chem 49:417–423

    Article  CAS  PubMed  Google Scholar 

  11. Sayyafi M, Seyyedhamzeh M, Khavasi HR, Bazgir A (2008) One-pot, three-component route to 2H-indazolo[2,1-b]phthalazinetriones. Tetrahedron 64:2375–2378

    Article  CAS  Google Scholar 

  12. Shaterian HR, Hosseinian A, Ghashang M (2009) Reusable silica supported poly phosphoric acid catalyzed three-component synthesis of 2H-indazolo[2,1-b]phthalazine-trione derivatives. ARKIVOC 2:59–67

    Article  Google Scholar 

  13. Ghahremanzadeh R, Imani Shakibaei G, Bazgir A (2008) An efficient one-pot synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives. Synlett 8:1129–1132

    Google Scholar 

  14. Nabid MR, Tabatabaei Rezaei SJ, Ghahremanzadeh R, Bazgir A (2010) Ultrasound-assisted one-pot, three-component synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones. Ultrason Sonochem 17:159–161

    Article  CAS  PubMed  Google Scholar 

  15. Khurana JM, Magoo D (2009) Efficient one-pot synthesis of 2H-indazolo[2,1-b] phthalazinetriones by catalytic H2SO4 in water-ethanol or ionic liquid. Tetrahedron Lett 50:7300–7303

    Article  CAS  Google Scholar 

  16. Wang HJ, Zhang XN, Zhang ZH (2010) Highly efficient three-component synthesis of 1H-indazolo[1,2-b]phthalazinetrione derivatives catalyzed by heteropolyacids. Monatsh Chem 141:425–430

    Article  CAS  Google Scholar 

  17. Shaterian HR, Khorami F, Amirzadeh A, Doostmohammadi R, Ghashang M (2009) Preparation of heterocyclic containing phthalazine skeletons: 2H-indazolo[2,1-b]-phthalazine-1,6,11(13H)-triones. J Iran Chem Res 2:57–62

    Google Scholar 

  18. Shaterian HR, Ghashang M, Feyzi M (2008) Silica sulfuric acid as an efficient catalyst for the preparation of 2H-indazolo[2,1-b]phthalazine-triones. Appl Catal A Gen 345:128–133

    Article  CAS  Google Scholar 

  19. Mulik AG, Chandam DR, Patil DR, Patil PP, Mulik GN, Salunkhe ST, Deshmukh MB (2015) Protic ionic liquids: a lucid, rational tool for synthesis of phthalazinediones, quinoxalines and benzopyrans. Res Chem Intermed 41:10085–10096

    Article  CAS  Google Scholar 

  20. Amirmahani N, Mahmoodi NO, Malakootian M, Pardakhty A (2022) [TBP]2SO4 ionic liquid catalyst for 4MCR of pyridazinoindazole, indazolophthalazine and pyrazolophthalazine derivatives. Mol Divers 26:15–25

    Article  CAS  PubMed  Google Scholar 

  21. Daneshvar N, Shirini F, Langarudi MSN, Karimi-Chayjani R (2018) Taurine as a green bio-organic catalyst for the preparation of bio-active barbituric and thiobarbituric acid derivatives in water media. Bioorg Chem 77:68–73

    Article  CAS  PubMed  Google Scholar 

  22. Shirini F, Langarudi MSN, Daneshvar N (2017) Preparation of a new DABCO-based ionic liquid [H2-DABCO][H2PO4]2} and its application in the synthesis of tetrahydro-benzo[b]pyran and pyrano[2,3-d]pyrimidinone derivatives. J Mol Liq 234:268–278

    Article  CAS  Google Scholar 

  23. Mashhadinezhad M, Shirini F, Mamaghani M (2018) Nanoporous Na+-montmorillonite perchloric acid as an efficient heterogeneous catalyst for synthesis of merocyanine dyes based on isoxazolone and barbituric acid. Microporous Mesoporous Mater 262:269–282

    Article  CAS  Google Scholar 

  24. Shirini F, Langarudi MSN, Daneshvar N, Jamasbi N, Irankhah-Khanghah M (2018) Preparation and characterization of [H2-DABCO][ClO4]2 as a new member of DABCO-based ionic liquids for the synthesis of pyrimido[4,5-b]quinoline and pyrimido[4,5-d]- pyrimidine derivatives. J Mol Struct 1161:366–382

    Article  CAS  Google Scholar 

  25. Daneshvar N, Nasiri M, Shirzad M, Langarudi MSN, Shirini F, Tajik H (2018) The introduction of two new imidazole-based bis-dicationic Bronsted acidic ionic liquids and comparison of their catalytic activity in the synthesis of barbituric acid derivatives. New J Chem 42:9744–9756

    Article  CAS  Google Scholar 

  26. Turhan K (2019) One-pot synthesis of substituted phthalazine-5,10-dione derivatives in the presence of triflate catalyst. J Inst Sci Technol 9:468–478

    Google Scholar 

  27. Hamidinasab M, Bodaghifard MA, Mobinikhaledi A (2020) Green synthesis of 1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile derivatives using a new bifunctional base-ionic liquid hybrid magnetic nanocatalyst. Appl Organomet Chem 34:e5386

    Article  CAS  Google Scholar 

  28. Kolsepatil SR, Sapkal AV, Chandole S, Lingampalle DL (2019) One-pot synthesis of pyrazolophthalazinedione derivatives under microwave irradiation. Rasayan J Chem 12:415–420

    Article  CAS  Google Scholar 

  29. Lashkari M, Mohamadpour F, Maghsoodlou MT, Heydari R, Hazeri N (2020) Uric acid as a naturally biodegradable and reusable catalyst for the convenient and eco-safe synthesis of biologically active pyran annulated heterocyclic systems. Polycycl Aromat Compd 42(4):1358–1374

    Article  Google Scholar 

  30. El-Rayes SM, El-Enany G, Ali IAI, Ibrahim W, Nafie MS (2022) synthesis of novel phthalazinedione-based derivatives with promising cytotoxic, anti-bacterial, and molecular docking studies as vegfr2 inhibitors. ACS Omega. https://doi.org/10.1021/acsomega.2c03182

    Article  PubMed  PubMed Central  Google Scholar 

  31. Sabour FH, Naser-Esfahani M, Mohammadpoor-Baltok I, Tangestaninejad S, Moghadam M, Mirkhani V (2018) A convenient approach for the synthesis of various derivatives of pyrazolo[1,2-b]phthalazinediones in the presence of an efficient supported basic ionic liquid at ambient temperature and solvent-free media. J Iran Chem Soc 15:671–683

    Article  Google Scholar 

  32. Kidwai M, Chauhan R (2014) A Rapid and an efficient route to the one-pot, multicomponent synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione ring systems. J Heterocycl Chem 51:1689–1696

    Article  CAS  Google Scholar 

  33. Mulika A, Deshmukha M, Chandama D, Patilb P, Jagdalea S, Patila D, Sankpala S (2013) Glycerol-promoted catalyst-free one-pot three component synthesis of 1H-pyrazolo[1,2-b]phthalazinediones. Der Pharm Chem 5:19–23

    Google Scholar 

  34. Safaei-Ghomi J, Shahbazi-Alavi H, Ziarati A, Teymuri R, Saberi MR (2014) A highly flexible green synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones with CuI nanoparticles as catalyst under solvent-free conditions. Chin Chem Lett 25:401–405

    Article  CAS  Google Scholar 

  35. Shaterian HR, Mohammadnia M (2014) Mild preparation of 1H-pyrazolo[1,2-b]-phthalazine-5,10-dione derivatives with magnetic Fe3O4 nanoparticles coated by (3-aminopropyl)triethoxysilane as catalyst under ambient and solvent-free conditions. Res Chem Intermed 40:371–383

    Article  CAS  Google Scholar 

  36. Mohamadpour F (2020) Carboxymethyl cellulose (CMC) as a recyclable green catalyst promoted eco-friendly protocol for the solvent-free synthesis of 1H-pyrazolo[1,2-b]-phthalazine-5,10-dione derivatives. Polycycl Aromat Compd 42(4):1091–1102

    Article  Google Scholar 

Download references

Acknowledgements

The authors are grateful to the Bu-Ali Sina University, Hamedan Iran, for the support of this work.

Author information

Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran

    Seyyed Sajjad Oliaei & Davood Habibi

  2. Social Determinants of Health Research Center, Saveh University of Medical Sciences, Saveh, Iran

    Somayyeh Heydari

  3. Department of Biology, College of Science, Bu-Ali Sina University, Hamedan, 6517838683, Iran

    Roya Karamian

  4. Department of Microbiology, School of Biology, College of Science, University of Tehran, Tehran, Iran

    Shokufeh Ghasemian Sorboni

Authors
  1. Seyyed Sajjad Oliaei
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Davood Habibi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Somayyeh Heydari
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Roya Karamian
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Shokufeh Ghasemian Sorboni
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Davood Habibi.

Ethics declarations

Conflict of interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

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 (DOCX 3044 kb)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Oliaei, S.S., Habibi, D., Heydari, S. et al. Unexpected synthesis of 4-(4,5-dihydro-1H-imidazol-2-ylsulfanyl)butyl-H-sulfite as a catalyst for the synthesis of pyrazolophthalazines. Mol Divers 27, 2453–2464 (2023). https://doi.org/10.1007/s11030-022-10563-w

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11030-022-10563-w

Keywords

Search

Navigation