Skip to main content
SpringerLink
Log in

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

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

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.

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

References

  1. Donnelly DMX, Boland GM (1995) Isoflavonoids and neoflavonoids: naturally occurring O-heterocycles. Nat Prod Rep 12: 321–338. doi:10.1039/np9951200321

    Article  CAS  Google Scholar 

  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

    Article  PubMed  CAS  Google Scholar 

  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

    Article  PubMed  CAS  Google Scholar 

  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. 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: 1813–1815

    CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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: 3142–3152

    CAS  Google Scholar 

  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. 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

    Article  PubMed  CAS  Google Scholar 

  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. 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

    Article  PubMed  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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. 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

    Article  PubMed  CAS  Google Scholar 

  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

    Article  PubMed  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  PubMed  CAS  Google Scholar 

  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

    Article  PubMed  CAS  Google Scholar 

  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

    Article  PubMed  CAS  Google Scholar 

  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

    Article  PubMed  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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-A

    Google Scholar 

  23. Terrett NK (1998) Combinatorial chemistry. Oxford University Press, New York

    Google Scholar 

  24. Dömling A (2006) Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev 106: 17–89. doi:10.1021/cr0505728

    Article  PubMed  CAS  Google Scholar 

  25. Zhu J, Bienayme H (2005) Multicomponent reactions. Wiley-VCH, Weinheim

    Google Scholar 

  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

    Article  PubMed  CAS  Google Scholar 

  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

    Article  PubMed  CAS  Google Scholar 

  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

    Article  PubMed  CAS  Google Scholar 

  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

    Article  PubMed  CAS  Google Scholar 

  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

    Article  PubMed  CAS  Google Scholar 

  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

    Article  PubMed  CAS  Google Scholar 

  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

    Article  PubMed  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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. 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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  37. McNab H (1978) Meldrum’s acid. Chem Soc Rev 7: 345–358. doi:10.1039/cs9780700345

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  Google Scholar 

  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: 891–893

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Shahid Beheshti University, P. O. Box 19396-4716, Tehran, Iran

    Ahmad Shaabani, Afshin Sarvary, Ebrahim Soleimani, Ali Hossein Rezayan & Marjan Heidary

Authors
  1. Ahmad Shaabani
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Afshin Sarvary
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ebrahim Soleimani
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ali Hossein Rezayan
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Marjan Heidary
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ahmad Shaabani.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shaabani, A., Sarvary, A., Soleimani, E. et al. A novel method for the synthesis of substituted 3,4-dihydrocoumarin derivatives via isocyanide-based three-component reaction. Mol Divers 12, 197–202 (2008). https://doi.org/10.1007/s11030-008-9090-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11030-008-9090-z

Keywords

Search

Navigation