Skip to main content
SpringerLink
Log in

A facile and regioselective one-pot synthesis of novel pyrazolo[1\('\),5\('\):1,2]pyrrolo[3,4-b]quinoline-2,3-dicarboxylate hybrids via intramolecular Wittig reaction

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

Abstract

The regioselective syntheses of novel pyrazolo[1\('\),5\('\):1,2]pyrrolo[3,4-b]quinoline-2,3-dicarboxylates (6a–l) from pyrrolo([3,4-b]quinolin-2(3H)-yl)benzamides through an intramolecular Wittig reaction are described. This protocol takes advantages of mild conditions, simple workup and high yield which make this method attractive for the synthesis of these hybrid of pyrazolo[1\('\),5\('\):1,2]pyrrolo[3,4-b]quinolines.

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
Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Kolodiazhnyi OI (1999) Phosphorus ylides: chemistry and application in organic synthesis. Wiley, New York

    Book  Google Scholar 

  2. Maryanoff BE, Reitz AB (1989) The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects. Chem Rev 89:863–927. doi:10.1021/cr00094a007

    Article  CAS  Google Scholar 

  3. Zbiral E (1974) Synthesen von Heterocyclen mit Hilfe von Alkylidenphosphoranen, Phosphin-imiden, Vinylphosphonium-salzen und Vinylphosphin-oxiden. Synthesis. doi:10.1055/s-1974-23432

  4. Ferrer P, Avendaño C, Söllhuber M (1995) Synthesis of 5,8-dimethoxy-2(1H)-quinolinones by intramolecular Wittig reaction. Liebigs Annalen 1995:1895–1899. doi:10.1002/jlac.1995199510266

    Article  Google Scholar 

  5. Becker KB (1980) Cycloalkenes by intramolecular wittig reaction. Tetrahedron 36:1717–1745. doi:10.1016/0040-4020(80)80068-8

    Article  CAS  Google Scholar 

  6. Noshiranzadeh N, Ramazani A (2008) The reaction of phenylhydrazine with sterically congested stabilized phosphorus ylides in the presence of silica gel powder in solvent-free conditions: a novel synthesis of fully substituted pyrazole derivatives. Phosphorus Sulfur Silicon Relat Elem 183:1109–1115. doi:10.1080/10426500701569448

    Article  CAS  Google Scholar 

  7. Ziyaadini M, Maghsoodlou MT, Hazeri N, Habibi-Khorassani SM (2012) Synthesis and dynamic 1H NMR study around the carbon–carbon double bond in the new stable phosphorus ylides derived from the reaction between hexamethyl phosphorous triamide and dimethyl acetylenedicarboxylate in the presence of NH-heterocyclic compounds. Heteroatom Chem 23:131–137. doi:10.1002/hc.20761

    Article  CAS  Google Scholar 

  8. Heydari R, Hazeri N, Maghsoodlou MT, Khorassani SMH, Marandi G, Maleki N, Kabiri R, Soleymani BG (2010) Solvent effects on the chemoselectivity of stable phosphorus ylides involving a sulfonamide. Phosphorus Sulfur Silicon Relat Elem 185:2135–2141. doi:10.1080/10426500903530883

    Article  CAS  Google Scholar 

  9. Kumar S, Bawa S, Gupta H (2009) Biological activities of quinoline derivatives. Mini Rev Med Chem 9:1648–1654. doi:10.2174/138955709791012247

    Article  CAS  PubMed  Google Scholar 

  10. Musiol R, Serda M, Hensel-Bielowka S, Polanski J (2010) Quinoline-based antifungals. Curr Med Chem 17:1960–1973. doi:10.2174/092986710791163966

    Article  CAS  PubMed  Google Scholar 

  11. Solomon VR, Lee H (2009) Chloroquine and its analogs: a new promise of an old drug for effective and safe cancer therapies. Eur J Pharmacol 625:220–233. doi:10.1016/j.ejphar.2009.06.063

    Article  CAS  PubMed  Google Scholar 

  12. Fourtillan JB, Fourtillan M, Jacquesy JC, Karam O, Zunino F, Jouannetaud MP (2000) Nouveaux derives de pyrrolo-(3,4-b)quinoleine, leur procede de preparation et leur utilisation a titre de medicament. World Patent WO2000064897

  13. Wang H, Ganesan A (1998) Total synthesis of the cytotoxic alkaloid luotonin A. Tetrahedron Lett 39:9097–9098. doi:10.1016/S0040-4039(98)02004-8

    Article  CAS  Google Scholar 

  14. Jayabal K, Paramasivan TP (2014) An expedient four-component domino protocol for the regioselective synthesis of highly functionalized pyranopyrazoles and chromenopyrazoles via nitroketene-N,S-acetal chemistry under solvent-free condition. Tetrahedron Lett 55:2010–2014. doi:10.1016/j.tetlet.2014.02.019

    Article  CAS  Google Scholar 

  15. Fortunak JMD, Mastrocola AR, Mellinger M, Sisti NJ, Wood JL, Zhuang Z-P (1996) Novel syntheses of camptothecin alkaloids, part I. Intramolecular [4+2] cycloadditions of N-arylimidates and 4H-3,1-benzoxazin-4-ones as 2-aza-1,3-dienes. Tetrahedron Lett 37:5679–5682. doi:10.1016/0040-4039(96)01204-X

    Article  CAS  Google Scholar 

  16. Yadav JS, Sarkar S, Chandrasekhar S (1999) A convergent total synthesis of mappicine ketone: a leading antiviral compound. Tetrahedron 55:5449–5456. doi:10.1016/S0040-4020(99)00191-X

  17. Sachse A, Penkova L, Noël G, Dechert S, Varzatskii OA, Fritsky IO, Meyer F (2008) Efficient syntheses of some versatile 3,5-bifunctional pyrazole building blocks. Synthesis 2008:800–806. doi:10.1055/s-2008-1032180

    Article  Google Scholar 

  18. Dvorak CA, Rudolph DA, Ma S, Carruthers NI (2005) Palladium-catalyzed coupling of pyrazole triflates with arylboronic acids. J Org Chem 70:4188–4190. doi:10.1021/jo0477897

    Article  CAS  PubMed  Google Scholar 

  19. Yavari I, Nematpour M (2012) Tandem synthesis of highly functionalized pyrazole derivatives from terminal alkynes, sulfonyl azides, diethyl azadicarboxylate, and sodium arylsulfinates. Mol Divers 16:651–657. doi:10.1007/s11030-012-9393-y

    Article  CAS  PubMed  Google Scholar 

  20. Konkala VS, Dubey PK (2017) Urea/thiourea: efficient, inexpensive and reusable catalysts for the synthesis of pyrazole derivatives with 2-iminothiazolidin-4-one and 2,4-thiazolidinediones under solvent-free conditions. Mol Divers 21:283–291. doi:10.1007/s11030-016-9719-2

    Article  CAS  PubMed  Google Scholar 

  21. Katritzky AR, Lagowski JM (1984) 4.01—structure of five-membered rings with two or more heteroatoms. In: Katritzky AR, Rees CW (eds) Comprehensive heterocyclic chemistry. Pergamon, Oxford, pp 1–38. doi:10.1016/B978-008096519-2.00069-2

  22. Elguero J, Goya P, Jagerovic N, Silva AMS (2002) Targets in heterocyclic systems, vol 6. Italian Society of Chemistry, Rome

    Google Scholar 

  23. Fustero S, Sánchez-Roselló M, Barrio P, Simón-Fuentes A (2011) From 2000 to mid-2010: a fruitful decade for the synthesis of pyrazoles. Chem Rev 111:6984–7034. doi:10.1021/cr2000459

    Article  CAS  PubMed  Google Scholar 

  24. Janin YL (2012) Preparation and chemistry of 3/5-halogenopyrazoles. Chem Rev 112:3924–3958. doi:10.1021/cr200427q

    Article  CAS  PubMed  Google Scholar 

  25. Thaher BA, Arnsmann M, Totzke F, Ehlert JE, Kubbutat MHG, Schächtele C, Zimmermann MO, Koch P, Boeckler FM, Laufer SA (2012) Tri- and tetrasubstituted pyrazole derivates: regioisomerism switches activity from p38MAP kinase to important cancer kinases. J Med Chem 55:961–965. doi:10.1021/jm201391u

    Article  PubMed  Google Scholar 

  26. Claudio V-J, Amanda D, Vanderlan da Silva B, Eliezer JB, Carlos Alberto Manssour F (2007) Molecular hybridization: a useful tool in the design of new drug prototypes. Curr Med Chem 14:1829–1852. doi:10.2174/092986707781058805

    Article  Google Scholar 

  27. Rad MNS, Behrouz S, Behrouz M, Sami A, Mardkhoshnood M, Zarenezhad A, Zarenezhad E (2016) Design, synthesis and biological evaluation of novel 1,2,3-triazolyl [Formula: see text]-hydroxy alkyl/carbazole hybrid molecules. Mol Divers 20:705–718. doi:10.1007/s11030-016-9678-7

    Article  CAS  PubMed  Google Scholar 

  28. Singh M, Kaur M, Chadha N, Silakari O (2016) Hybrids: a new paradigm to treat Alzheimer’s disease. Mol Divers 20:271–297. doi:10.1007/s11030-015-9628-9

    Article  CAS  PubMed  Google Scholar 

  29. Mazzoni O, Esposito G, Diurno MV, Brancaccio D, Carotenuto A, Grieco P, Novellino E, Filippelli W (2010) Synthesis and pharmacological evaluation of Some 4-Oxo-quinoline-2-carboxylic acid derivatives as anti-inflammatory and analgesic agents. Arch Pharm 343:561–569. doi:10.1002/ardp.201000016

    Article  CAS  Google Scholar 

  30. Patil NT, Raut VS (2010) Cooperative catalysis with metal and secondary amine: synthesis of 2-substituted quinolines via addition/cycloisomerization cascade. J Org Chem 75:6961–6964. doi:10.1021/jo101103a

    Article  CAS  PubMed  Google Scholar 

  31. Becke AD (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648–5652. doi:10.1063/1.462066

    Article  CAS  Google Scholar 

  32. Yang LW, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785–789. doi:10.1103/PhysRevB.37.785

    Article  Google Scholar 

  33. Francl MM, Pietro WJ, Hehre WJ, Binkley JS, DeFrees DJ, Pople JA, Gordon MS (1982) Self-consistent molecular orbital methods. 23. A polarization-type basis set for 2nd-row elements. J Chem Phys 77:3654–3665. doi:10.1063/1.444267

    Article  CAS  Google Scholar 

  34. Schmidt MW, Baldridge KK, Boatz JA, Elbert ST, Gordon MS, Jensen JH, Koseki S, Matsunaga N, Nguyen KA, Su S, Windus TL, Dupuis M, Montgomery JA (1993) General atomic and molecular electronic structure system. J Comput Chem 14:1347–1363. doi:10.1002/jcc.540141112

    Article  CAS  Google Scholar 

  35. Granovsky AA. Firefly version 8.1.0. http://classic.chem.msu.su/gran/firefly/index.html

Download references

Acknowledgements

The authors are grateful to the University of Mohaghegh Ardabili for the financial support and the laboratories of Shahid Beheshti, Tabriz and Atatürk Universities for analyzing our products.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Mohaghegh Ardabili, Ardabil, 56199-11367, Iran

    Tahere Hosseyni Largani, Gholamhasan Imanzadeh & Amir Nasser Shamkhali

  2. Department of Chemistry, Faculty of Science, Urmia University, Urmia, 57159, Iran

    Nader Noroozi Pesyan

  3. Department of Chemistry, Faculty of Science, Atatürk University, Erzurum, 25240, Turkey

    Ertan Şahin

  4. Department of Chemistry, ShahidBeheshti University, Tehran, 1983963113, Iran

    Behrouz Notash

Authors
  1. Tahere Hosseyni Largani
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Gholamhasan Imanzadeh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Nader Noroozi Pesyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ertan Şahin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Amir Nasser Shamkhali
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Behrouz Notash
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Gholamhasan Imanzadeh.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (docx 19097 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Largani, T.H., Imanzadeh, G., Pesyan, N.N. et al. A facile and regioselective one-pot synthesis of novel pyrazolo[1\('\),5\('\):1,2]pyrrolo[3,4-b]quinoline-2,3-dicarboxylate hybrids via intramolecular Wittig reaction. Mol Divers 22, 37–46 (2018). https://doi.org/10.1007/s11030-017-9784-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11030-017-9784-1

Keywords

Search

Navigation