ULTRASOUND ASSISTED GREEN SYNTHESIS OF 2-FURAN-2-YL-4H-CHROMEN-4-ONES FROM CHALCONES
DOI:
https://doi.org/10.22159/ijcpr.2020v12i3.38312Keywords:
Chromen-4-one, Chalcones, Iodine, Ultrasound irradiationAbstract
Objective: To report the ultrasound-assisted synthesis of some bioactive 2-furan-2-yl-4H-chromen-4-one derivatives
Methods: Oxidative cyclization of chalcones using iodine in dimethyl sulfoxide for the synthesis.
Results: Some bioactive 2-furan-2-yl-4H-chromen-4-one derivatives were synthesized from corresponding chalcones in the presence of iodine in dimethyl sulfoxide under ultrasound irradiation at ambient reaction conditions.
Conclusion: The use of ultrasound irradiation gave the advantages of higher yields, lower reaction time and simplicity compared to conventional methods for the synthesis of 2-furan-2-yl-4H-chromen-4-one derivatives.
Downloads
Download data is not yet available.
References
1. Puri S, Kaur B, Parmar A, Kumar H. Applications of ultrasound in organic synthesis-a green approach. Curr Org Chem 2013;17:1790-828.
2. Cintas P, Luche JL. Green chemistry: the sonochemical approach. Green Chem 1999;1:115-25.
3. Saengchantara ST, Wallace TW. Chromanols, chromanones, and chromones. Nat Prod Rep 1986;3:465-75.
4. Cottiglia F, Dhanapal B, Sticher O, Heilmann J. New chromanone acids with antibacterial activity from Calophyllum brasiliense. J Nat Prod 2004;67:537-41.
5. Horton DA, Bourne GT, Smythe ML. The combinatorial synthesis of bicyclic privileged structures or privileged substructures. Chem Rev 2003;103:893-930.
6. Bhat AS, Whetstone JL, Brueggemeier RW. Novel synthetic routes suitable for constructing benzopyrone combinatorial libraries. Tetrahedron Lett 1999;40:2469-72.
7. Bauvois B, Puiffe ML, Bongui JB, Paillat S, Monneret C, Dauzonne D. Synthesis and biological evaluation of novel flavones-8-acetic acid derivatives as reversible inhibitors of aminopeptidase N/CD13. J Med Chem 2003;46:3900-13.
8. Kim HP, Son KH, Chang HW, Kang SS. Anti-inflammatory plant flavonoids and cellular action mechanisms. J Pharmacol Sci 2004;96:229-45.
9. Gaspar A, Matos MJ, Garrido J, Uriarte E, Borges F. Chromone: a valid scaffold in medicinal chemistry. Chem Rev 2014;114:4960-92.
10. Friden Saxin M, Pemberton N, Andersson KD, Dyrager C, Friberg A, Grotli M, et al. Synthesis of 2-alkylsubstituted chromone derivatives using microwave irradiation. J Org Chem 2009;74:2755-9.
11. Dahlen K, Wallen EAA, Grotli M, Luthman K. Synthesis of 2,3,6,8-tetrasubstituted chromone scaffolds. J Org Chem 2006;71:6863-71.
12. Dahlen K, Grotli M, Luthman K. A scaffold approach to 3,6,8-trisubstituted flavones. Synth Lett 2006;6:897-900.
13. Wallen EAA, Dahlen K, Grotli M, Luthman K, Synthesis of 3-aminomethyl-2-aryl-8-bromo-6-chlorochromones. Org Lett 2007;9:389-91.
14. Ankner T, Friden Saxin M, Pemberton N, Seifert T, Grotli M, Luthman K, et al. KHMDS enhanced SmI2-mediated reformatsky type ?-cyanation. Org Lett 2010;12:2210-3.
15. Friden Saxin M, Seifert T, Landergren MR, Suuronen T, Lahtela Kakkonen M, Jarho EM, et al. Synthesis and evaluation of substituted chroman-4-one and chromone derivatives as sirtuin 2 selective inhibitors. J Med Chem 2012;55:7104-13.
16. Sylvie, Richard DF, John H, Alex K, Nicholas JL. Potent antimitotic and cell growth inhibitory properties of substituted chalcones. Bioorg Med Chem Lett 1998;8:1051-6.
17. Shastri RA. Synthesis and antimicrobial activity of some novel pyrazoline and flavones derivatives derived from furan chalcone. World J Pharm Res 2015;4:642-51.
18. Khandapu BK, Mutchu BR, Thripuram VD, Polam N, Anandam R, Navudu R, et al. Reaction of O-methylated flavones with semicarbazide: serendipitous selective demethylation. Org Commun 2018;11:116-22.
2. Cintas P, Luche JL. Green chemistry: the sonochemical approach. Green Chem 1999;1:115-25.
3. Saengchantara ST, Wallace TW. Chromanols, chromanones, and chromones. Nat Prod Rep 1986;3:465-75.
4. Cottiglia F, Dhanapal B, Sticher O, Heilmann J. New chromanone acids with antibacterial activity from Calophyllum brasiliense. J Nat Prod 2004;67:537-41.
5. Horton DA, Bourne GT, Smythe ML. The combinatorial synthesis of bicyclic privileged structures or privileged substructures. Chem Rev 2003;103:893-930.
6. Bhat AS, Whetstone JL, Brueggemeier RW. Novel synthetic routes suitable for constructing benzopyrone combinatorial libraries. Tetrahedron Lett 1999;40:2469-72.
7. Bauvois B, Puiffe ML, Bongui JB, Paillat S, Monneret C, Dauzonne D. Synthesis and biological evaluation of novel flavones-8-acetic acid derivatives as reversible inhibitors of aminopeptidase N/CD13. J Med Chem 2003;46:3900-13.
8. Kim HP, Son KH, Chang HW, Kang SS. Anti-inflammatory plant flavonoids and cellular action mechanisms. J Pharmacol Sci 2004;96:229-45.
9. Gaspar A, Matos MJ, Garrido J, Uriarte E, Borges F. Chromone: a valid scaffold in medicinal chemistry. Chem Rev 2014;114:4960-92.
10. Friden Saxin M, Pemberton N, Andersson KD, Dyrager C, Friberg A, Grotli M, et al. Synthesis of 2-alkylsubstituted chromone derivatives using microwave irradiation. J Org Chem 2009;74:2755-9.
11. Dahlen K, Wallen EAA, Grotli M, Luthman K. Synthesis of 2,3,6,8-tetrasubstituted chromone scaffolds. J Org Chem 2006;71:6863-71.
12. Dahlen K, Grotli M, Luthman K. A scaffold approach to 3,6,8-trisubstituted flavones. Synth Lett 2006;6:897-900.
13. Wallen EAA, Dahlen K, Grotli M, Luthman K, Synthesis of 3-aminomethyl-2-aryl-8-bromo-6-chlorochromones. Org Lett 2007;9:389-91.
14. Ankner T, Friden Saxin M, Pemberton N, Seifert T, Grotli M, Luthman K, et al. KHMDS enhanced SmI2-mediated reformatsky type ?-cyanation. Org Lett 2010;12:2210-3.
15. Friden Saxin M, Seifert T, Landergren MR, Suuronen T, Lahtela Kakkonen M, Jarho EM, et al. Synthesis and evaluation of substituted chroman-4-one and chromone derivatives as sirtuin 2 selective inhibitors. J Med Chem 2012;55:7104-13.
16. Sylvie, Richard DF, John H, Alex K, Nicholas JL. Potent antimitotic and cell growth inhibitory properties of substituted chalcones. Bioorg Med Chem Lett 1998;8:1051-6.
17. Shastri RA. Synthesis and antimicrobial activity of some novel pyrazoline and flavones derivatives derived from furan chalcone. World J Pharm Res 2015;4:642-51.
18. Khandapu BK, Mutchu BR, Thripuram VD, Polam N, Anandam R, Navudu R, et al. Reaction of O-methylated flavones with semicarbazide: serendipitous selective demethylation. Org Commun 2018;11:116-22.
Published
15-05-2020
How to Cite
KAKADE, G. K., and S. G. VEDPATHAK. “ULTRASOUND ASSISTED GREEN SYNTHESIS OF 2-FURAN-2-YL-4H-CHROMEN-4-ONES FROM CHALCONES”. International Journal of Current Pharmaceutical Research, vol. 12, no. 3, May 2020, pp. 84-86, doi:10.22159/ijcpr.2020v12i3.38312.
Issue
Section
Original Article(s)
