Advertisement

Molecular Diversity

, 12:197 | Cite as

A novel method for the synthesis of substituted 3,4-dihydrocoumarin derivatives via isocyanide-based three-component reaction

  • Ahmad Shaabani
  • Afshin Sarvary
  • Ebrahim Soleimani
  • Ali Hossein Rezayan
  • Marjan Heidary
Short Communication

Abstract

A new one-pot procedure for the efficient synthesis of novel 3,4-dihydrocoumarin derivatives using commercially available substituted 2-hydroxybenzaldehydes, Meldrum’s acid, and isocyanides by a three-component condensation reaction in dichloromethane at room temperature without using any catalysts and activation was developed.

Keywords

Isocyanide 3,4-Dihydrocoumarin derivatives Multi-component reactions 2-Hydroxybenzaldehydes 

References

  1. 1.
    Donnelly DMX, Boland GM (1995) Isoflavonoids and neoflavonoids: naturally occurring O-heterocycles. Nat Prod Rep 12: 321–338. doi: 10.1039/np9951200321 CrossRefGoogle Scholar
  2. 2.
    Posakony J, Hirao M, Stevens S, Simon JA, Bedalov A (2004) Inhibitors of Sir2: evaluation of splitomicin analogues. J Med Chem 47: 2635–2644. doi: 10.1021/jm030473r PubMedCrossRefGoogle Scholar
  3. 3.
    Kumar A, Singh BK, Tyagi R, Jain SK, Sharma SK, Prasad AK et al (2005) Mechanism of biochemical action of substituted 4-methylcoumarins. Part 11: comparison of the specificities of acetoxy derivatives of 4-methylcoumarin and 4-phenylcoumarin to acetoxycoumarins: protein transacetylase. Bioorg Med Chem 13: 4300–4305. doi: 10.1016/j.bmc.2005.04.023 PubMedCrossRefGoogle Scholar
  4. 4.
    Roelens F, Huvaere K, Dhooge W, Cleemput MV, Comhaire F, Keukeleire DD (2005) Regioselective synthesis and estrogenicity of ( ± )-8-alkyl-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarins. Eur J Med Chem 40:1042–1151. doi: 10.1016/j.ejmech.2005.04.010 Google Scholar
  5. 5.
    Iinuma M, Tanaka T, Mizuno M, Katsuzaki T, Ogawa H (1989) Structure-activity correlation of flavonoids for inhibition of bovin lens aldose reductase. Chem Pharm Bull (Tokyo) 37: 1813–1815Google Scholar
  6. 6.
    Takechi M, Tanaka Y, Takehara M, Nonaka GI, Nishioka I (1985) Structure and antiherpetic activity among the Tannins. Phytochemistry 24: 2245–2250. doi: 10.1016/S0031-9422(00)83018-6 CrossRefGoogle Scholar
  7. 7.
    Hsu FL, Nonaka GI, Nishioka I (1985) Tannins and related compounds. XXXI. Isolation and characterization of proanthocyanidins in kandelia candel (L.) DRUCE. Chem Pharm Bull Tokyo 33: 3142–3152Google Scholar
  8. 8.
    Speranza G, Morelli CF, Manitto P (2000) The michael reaction of N-cinnamoylazoles with phenols. A simple synthesis of 4-arylchroman-2-ones and 1-arylbenzo[f]chroman-3-ones. Synthesis 123–126. doi: 10.1055/s-2000-6233
  9. 9.
    Jia C, Piao D, Kitamura T, Fujiwara Y (2000) New method for preparation of coumarins and quinolinones via Pd-catalyzed intramolecular hydroarylation of C–C triple bonds. J Org Chem 65: 7516–7522. doi: 10.1021/jo000861q PubMedCrossRefGoogle Scholar
  10. 10.
    Lee JM, Tseng TH, Lee YJ (2001) An efficient synthesis of neoflavonoid antioxidants based on montmorillonite K-10 catalysis. Synthesis 2247–2254. doi: 10.1055/s-2001-18436
  11. 11.
    Li K, Foresee LN, Tunge JA (2005) Trifluoroacetic acid-mediated hydroarylation: synthesis of dihydrocoumarins and dihydroquinolones. J Org Chem 70: 2881–2883. doi: 10.1021/jo0477650 PubMedCrossRefGoogle Scholar
  12. 12.
    Aoki S, Amamoto C, Oyamada J, Kitamura T (2005) A convenient synthesis of dihydrocoumarins from phenols and cinnamic acid derivatives. Tetrahedron 61: 9291–9297. doi: 10.1016/j.tet.2005.07.062 CrossRefGoogle Scholar
  13. 13.
    Graham SR, Murphy JA, Kennedy AR (1999) Hypophosphite mediated carbon–carbon bond formation: total synthesis of epialboatrin and structural revision of alboatrin. J Chem Soc, Perkin Trans 1 3071–3073. doi: 10.1039/a907032j
  14. 14.
    Jia C, Piao D, Oyamada J, Lu W, Kitamura T, Fujiwara Y (2000) Efficient activation of aromatic C–H bonds for addition to C–C multiple bonds. Science 287: 1992–1995. doi: 10.1126/science.287.5460.1992 PubMedCrossRefGoogle Scholar
  15. 15.
    Ritleng V, Sirlin C, Pfeffer M (2002) Ru-, Rh-, and Pd-Catalyzed C–C bond formation involving C–H activation and addition on unsaturated substrates: reactions and mechanistic aspects. Chem Rev 102: 1731–1770. doi: 10.1021/cr0104330 PubMedCrossRefGoogle Scholar
  16. 16.
    Song CE, Jung D, Choung SY, Roh EJ, Lee S (2004) Dramatic enhancement of catalytic activity in an ionic liquid: highly practical friedel-crafts alkenylation of arenes with alkynes catalyzed by metal triflates. Angew Chem Int Ed 43: 6183–6185. doi: 10.1002/anie.200460292 CrossRefGoogle Scholar
  17. 17.
    Shi Z, He C (2004) Efficient functionalization of aromatic C–H bonds catalyzed by gold(III) under mild and solvent-free conditions. J Org Chem 69: 3669–3671. doi: 10.1021/jo0497353 PubMedCrossRefGoogle Scholar
  18. 18.
    Fillion E, Dumas AM, Kuropatawa BA, Malhotra NR, Sitler TC (2006) Yb(OTf)3-Catalyzed reactions of 5-alkylidene meldrum’s acids with phenols: one-pot assembly of 3,4-dihydrocoumarins, 4-chromanones, coumarins, and chromones. J Org Chem 71: 409–412. doi: 10.1021/jo052000t PubMedCrossRefGoogle Scholar
  19. 19.
    Youn SW, Pastine SJ, Sames D (2004) Ru(III)-Catalyzed cyclization of arene-alkene substrates via intramolecular electrophilic hydroarylation. Org Lett 6: 581–584. doi: 10.1021/ol036385i PubMedCrossRefGoogle Scholar
  20. 20.
    Dömling A (2002) Recent advances in isocyanide-based multicomponent chemistry. Curr Opin Chem Biol 6: 306–313. doi: 10.1016/S1367-5931(02)00328-9 PubMedCrossRefGoogle Scholar
  21. 21.
    Trost BM (1995) Atom economy—a challenge for organic synthesis: homogeneous catalysis leads the way. Angew Chem Int Ed Engl 34: 259–281. doi: 10.1002/anie.199502591 CrossRefGoogle Scholar
  22. 22.
    Bienayme H, Hulme C, Oddon G, Schmitt P (2000) Maximizing synthetic efficiency: multi-component transformations lead the way. Chem Eur J 6:3321–3329. doi:10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO;2-AGoogle Scholar
  23. 23.
    Terrett NK (1998) Combinatorial chemistry. Oxford University Press, New YorkGoogle Scholar
  24. 24.
    Dömling A (2006) Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev 106: 17–89. doi: 10.1021/cr0505728 PubMedCrossRefGoogle Scholar
  25. 25.
    Zhu J, Bienayme H (2005) Multicomponent reactions. Wiley-VCH, WeinheimGoogle Scholar
  26. 26.
    Lee D, Sello JK, Schreiber SL (2000) Pairwise use of complexity-generating reactions in diversity-oriented organic synthesis. Org Lett 2: 709–712. doi: 10.1021/ol005574n PubMedCrossRefGoogle Scholar
  27. 27.
    Sisko J, Kassick AJ, Mellinger M, Filan JJ, Allen A, Olsen MA (2000) An investigation of imidazole and oxazole syntheses using aryl-substituted tosmic reagents. J Org Chem 65: 1516–1524. doi: 10.1021/jo991782l PubMedCrossRefGoogle Scholar
  28. 28.
    Nair LG, Fraser-Reid B, Szardenings AK (2001) A versatile, three-component-reaction route to N-glycosylamines. Org Lett 3: 317–319. doi: 10.1021/ol000265i PubMedCrossRefGoogle Scholar
  29. 29.
    Sun X, Javier P, Zhao G, Bienayme H, Zu J (2001) A novel multicomponent synthesis of polysubstituted 5-aminooxazole and its new scaffold-generating reaction to pyrrolo[3,4-b]pyridine. Org Lett 3: 877–880. doi: 10.1021/ol007055q PubMedCrossRefGoogle Scholar
  30. 30.
    Shaabani A, Soleimani E, Rezayan AH, Sarvary A, Khavasi HR (2008) Novel isocyanide-based four-component reaction: a facile synthesis of fully substituted 3,4-dihydrocoumarin derivatives. Org Lett 10: 2581–2584. doi: 10.1021/ol800856e PubMedCrossRefGoogle Scholar
  31. 31.
    Shaabani A, Soleimani E, Sarvary A, Rezayan AH (2008) A simple and efficient approach to the synthesis of 4H-furo[3,4-b]pyrans via a three component reaction of isocyanides. Bioorg Med Chem Lett 18: 3968–3970. doi: 10.1016/j.bmcl.2008.06.014 PubMedCrossRefGoogle Scholar
  32. 32.
    Shaabani A, Soleimani E, Khavasi HR (2008) Synthesis of 1-aminoimidazo[5,1-a]isoquinolinium salts based on multicomponent reactions of isocyanides. J Comb Chem 10: 442–446. doi: 10.1021/cc700196h PubMedCrossRefGoogle Scholar
  33. 33.
    Shaabani A, Soleimani E, Rezayan AH (2007) A novel approach for the synthesis of aryl amides. Tetrahedron Lett 48: 6137–6141. doi: 10.1016/j.tetlet.2007.06.136 CrossRefGoogle Scholar
  34. 34.
    Shaabani A, Rezayan AH, Rahmati A, Sarvary A (2007) A novel isocyanide-based three-component condensation reaction: synthesis of fully substituted imino and spiroiminocyclopentenes. Synlett 1458–1460. doi: 10.1055/s-2007-980364
  35. 35.
    Shaabani A, Soleimani E, Khavasi HR (2007) An unexpected, novel, three-component reaction between isoquinoline, an isocyanide and strong CH-acids in water. Tetrahedron Lett 48: 4743–4747. doi: 10.1016/j.tetlet.2007.05.019 CrossRefGoogle Scholar
  36. 36.
    Maggi R, Bigi F, Carloni S, Mazzacani A, Sartori G (2001) Uncatalysed reactions in water: Part 2. Preparation of carboxycoumarins. Green Chem 3: 173–174. doi: 10.1039/b101822c CrossRefGoogle Scholar
  37. 37.
    McNab H (1978) Meldrum’s acid. Chem Soc Rev 7: 345–358. doi: 10.1039/cs9780700345 CrossRefGoogle Scholar
  38. 38.
    Bigi F, Carloni S, Ferrari L, Maggi R, Mazzacani A, Sartori G (2001) Palladium-catalyzed [3+2] cycloaddition of alkylidenecyclopropanes with imines. Tetrahedron Lett 42: 5203–5205. doi: 10.1016/S0040-4039(01)00978-9 CrossRefGoogle Scholar
  39. 39.
    Oikawa Y, Sugano K, Yonemitsu O (1978) Meldrum’s acid in organic synthesis. A general and versatile synthesis of. beta.-keto esters. J Org Chem 43: 2087–2088. doi: 10.1021/jo00404a066 CrossRefGoogle Scholar
  40. 40.
    Oikawa Y, Hirasawa H, Yonemitsu O (1978) Meldrum’s acid in organic synthesis. 1. A convenient one-pot synthesis of ethyl indolepropionates. Tetrahedron Lett 19: 1759–1762. doi: 10.1016/0040-4039(78)80037-9 CrossRefGoogle Scholar
  41. 41.
    Figueroa-Villar JD, Carneiro CL, Cruz ER (1992) Synthesis of 6-phenylaminofuro[2,3-d]pyrimidine-2,4(1H,3H)-diones from barbiturylbenzylidens and isonitriles. Heterocycles 34: 891–893CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V. 2008

Authors and Affiliations

  • Ahmad Shaabani
    • 1
  • Afshin Sarvary
    • 1
  • Ebrahim Soleimani
    • 1
  • Ali Hossein Rezayan
    • 1
  • Marjan Heidary
    • 1
  1. 1.Department of ChemistryShahid Beheshti UniversityTehranIran

Personalised recommendations