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New multicomponent approach for the synthesis of benzo[c]coumarin derivatives over MgO under solvent-free conditions

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Abstract

In this study, a three-component one-pot synthesis of select 5-amino-6-cyano-3-hydroxybenzo[c]coumarin compounds derived from salicylaldehydes, malononitrile, and ethyl acetoacetate is reported. The reaction is conducted on grinding over MgO at room temperature resulting in good yields.

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References

  1. Wessjohann LA, Ruijter E (2005) Macrocycles rapidly produced by multiple multicomponent reactions including bifunctional building blocks (MiBs). Mol Divers 9: 159–169. doi:10.1007/s11030-005-1313-y

    Article  PubMed  CAS  Google Scholar 

  2. Bienayme H, Hulme C, Oddon G, Schmitt P (2000) Reactivity of various four-coordinate aluminum alkyls towards dioxygen: evidence for spatial requirements in the insertion of an oxygen molecule into the Al–C bond. Chem Eur J 6: 3221–3227. doi:10.1002/1521-3765(20000901)6:17

    Article  Google Scholar 

  3. Shestopalov AM, Emeliyanova YM, Shestiopolov AA, Rodinovskaya IA, Niazimbetova AL, Evans DH (2002) One-step synthesis of substituted 6-amino-5-cyanospiro-4-(piperidine-4’)-2H,4H-dihydropyrazolo[3,4-b]pyrans. Org Lett 4: 423–425. doi:10.1021/o10102747

    Article  PubMed  CAS  Google Scholar 

  4. Bagley MC, Lubinu MC (2006) Microwave-assisted multicomponent reactions for the synthesis of heterocycles. Mol Divers 1: 31–58. doi:10.1007/7081_004

    CAS  Google Scholar 

  5. Bora U, Saikia A, Boruah RC (2003) A novel microwave-mediated one-pot synthesis of indolizines via a three-component reaction. Org Lett 5: 435–438. doi:10.1021/ol020238n

    Article  PubMed  CAS  Google Scholar 

  6. Dallinger D, Gorobets NY, Kappe CO (2003) High-throughput synthesis of N3-acylated dihydropyrimidines combining microwave-assisted synthesis and scavenging techniques. Org Lett 5: 1205–1208. doi:10.1021/ol034085v

    Article  PubMed  CAS  Google Scholar 

  7. Gelens E, De Kanter FJJ, Schmitz RF, Sliedregt LAJM, Steen BJV, Kruse CG, Leurs R, Groen MB, Orru RVA (2006) Efficient library synthesis of imidazoles using a multicomponent reaction and microwave irradiation. Mol Divers 10: 17–22. doi:10.1007/s11030-006-8695-3

    Article  PubMed  CAS  Google Scholar 

  8. Tanaka K, Toda F (2000) Solvent-free organic synthesis. Chem Rev 100: 1025–1074. doi:10.1021/cr940089p

    Article  PubMed  CAS  Google Scholar 

  9. Anastas PT, Warner JC (1998) Green chemistry: theory and practice. Oxford University Press, Oxford

    Google Scholar 

  10. Tanaka K, Kishigami S, Toda F (1991) Reformatsky and luche reaction in the absence of solvent. J Org Chem 56: 4333–4334. doi:10.1021/jo00013a055

    Article  CAS  Google Scholar 

  11. Toda F, Tanaka K, Hamai K (1990) Aldol condensations in the absence of solvent: acceleration of the reaction and enhancement of the stereoselectivity. J Chem Soc Perkin Trans 1: 3207–3209. doi:10.1039/P19900003207

    Article  Google Scholar 

  12. Toda F, Suzuki T, Higa S (1998) Solvent-free Dieckmann condensation reactions of diethyl adipate and pimelate. J Chem Soc Perkin Trans 1: 3521–3522. doi:10.1039/a805884i

    Article  Google Scholar 

  13. Ren Z-J, Cao W-G, Tong W-Q (2002) The Knoevenagel condensation reaction of aromatic aldehydes with malononitrile by grinding in the absence of solvents and catalysts. Synth Commun 32: 3475–3479. doi:10.1081/SCC-120014780

    Article  CAS  Google Scholar 

  14. Toda F, Kiyoshige K, Yagi M (1989) NaBH4 reduction of ketones in the solid state. Angew Chem Int Ed Engl 28: 320–321. doi:10.1002/anie.198903201

    Article  Google Scholar 

  15. Ren Z, Cao W, Tong W, Jin Z (2005) Solvent-free, one-pot synthesis of pyrano[2,3-c]pyrazole derivatives in the presence of KF·2H2O by grinding. Synth Commun 35: 2509–2513. doi:10.1080/00397910500212809

    Article  CAS  Google Scholar 

  16. Schmeyers T, Toda F, Boy J, Kaupp G (1998) Quantitative solid–solid synthesis of azomethines. J Chem Soc Perkin Trans 2: 989–994. doi:10.1039/a704633b

    Google Scholar 

  17. Manoj BG, Radha VJ (2006) A novel catalyst for the Knoevenagel condensation of aldehydes with malononitrile and ethyl cyanoacetate under solvent free conditions. Catal Commun 7: 931–935. doi:10.1016/j.catcom.2006.03.008

    Article  Google Scholar 

  18. Wang X-S, Zhou J-X, Zeng Z-S, Li Y-L, Shi D-Q, Tua S-J (2006) One-pot synthesis of pyrano[3,2-c]pyran derivatives catalyzed by KF/Al2O3. Arkivoke XI: 107–113

    Google Scholar 

  19. Babu NS, Pasha N, Venkateswara Rao KT, Sai Prasad PS, Lingaiah N (2008) A heterogeneous strong basic Mg/La mixed oxide catalyst for efficient synthesis of polyfunctionalized pyrans. Tetrahedron Lett 49: 2730–2733. doi:10.1016/j.tetlet.2008.02.154

    Article  CAS  Google Scholar 

  20. Murray RDH, Mendez J, Brown SA (1982) The natural coumarins: occurrence, chemistry and biochemistry. Wiley, New York

    Google Scholar 

  21. Othmer K (1979) Encyclopedia of chemical tecnology, 3rd edn. Wiley, New York, vol 7, pp 196–906; vol 16, pp 951–955; vol 4 p 15

  22. Hammad A, El-Sayed AS, Islam IE, Shafik N (1990) J Chem Soc Pax 12: 292 [Chem Abstr (1990) 115:71279s]

    CAS  Google Scholar 

  23. Kulkarni GM, Kulkarni HV, Patil VD, Shridhar DB, Laxmana M (1990) Rev Roum Chim 35: 549

    CAS  Google Scholar 

  24. Harvey RG, Cortex C, Ananthanarayan TP, Schmolka S (1988) A new coumarin synthesis and its utilization for the synthesis of polycyclic coumarin compounds with anticarcinogenic properties. J Org Chem 53: 3936–3943. doi:10.1021/jo00252a011

    Article  CAS  Google Scholar 

  25. Valizadeh H, Heravi MM, Amiri M (2009) Unexpected synthesis of N-methylbenzo[d]isoxazolium hydroxides under microwave irradiation conditions. Mol Divers published online doi:10.1007/s11030-009-9189-x

  26. Valizadeh H, Amiri M, Gholipour H (2009) Efficient and convenient method for the synthesis of isoxazoles in ionic liquid. J Heterocycl Chem 46: 108–110. doi:10.1002/jhet.20

    Article  CAS  Google Scholar 

  27. Valizadeh H, Shockravi A (2005) An efficient procedure for the synthesis of coumarin derivatives using TiCl4 as catalyst under solvent-free conditions. Tetrahedron Lett 46: 3501–3503. doi:10.1016/j.tetlet.2005.03.124

    Article  CAS  Google Scholar 

  28. Valizadeh H, Shockravi A (2009) Task-specific ionic liquid as reagent and reaction medium for the one-pot Horner–Wadsworth–Emmons–type reaction under microwave irradiation. Synth Commun 39: 4341–4349. doi:10.1080/00397910902898650

    Article  CAS  Google Scholar 

  29. Valizadeh H, Dinparast L (2009) Rapid, efficient, and room temperature synthesis of nitrones in excellent yields over MgO under solvent-free conditions. Heteroatom Chem 20: 177–181. doi:10.1002/hc.20527

    Article  CAS  Google Scholar 

  30. Valizadeh H, Fakhari A (2009) Facile, efficient, and eco-friendly synthesis of benzo[b]pyran-2-imines over MgO and transformation to the coumarin derivatives. J Heterocycl Chem 46: 1392–1395. doi:10.1002/jhet.265

    Article  CAS  Google Scholar 

  31. Valizadeh H, Vaghefi S (2009) One-Pot wittig and Knoevenagel reactions in ionic liquid as convenient methods for the synthesis of coumarin derivatives. Synth Commun 39: 1666–1678. doi:10.1080/00397910802573163

    Article  CAS  Google Scholar 

  32. Valizadeh H, Shockravi A (2009) Imidazolium-based phosphinite ionic liquid as reusable catalyst and solvent for one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-(thio)ones. Heteroatom Chem 20: 284–288. doi:10.1002/hc.20549

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, Azarbaijan University of Tarbiat Moallem, Tabriz, Iran

    Hassan Valizadeh & Ashraf Fakhari

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  1. Hassan Valizadeh
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  2. Ashraf Fakhari
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Correspondence to Hassan Valizadeh.

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Valizadeh, H., Fakhari, A. New multicomponent approach for the synthesis of benzo[c]coumarin derivatives over MgO under solvent-free conditions. Mol Divers 15, 233–237 (2011). https://doi.org/10.1007/s11030-010-9260-7

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  • DOI: https://doi.org/10.1007/s11030-010-9260-7

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