Research Article
BibTex RIS Cite
Year 2020, Volume: 3 Issue: 2, 80 - 85, 31.10.2020

Abstract

References

  • Akpınar DE, Ozgur M, Aslan H, Alagoz O, Oktemer A, Dal H, Hokelek T, Logoglu, E (2018). Synthesis, characterization, and investigations of antimicrobial activity of benzopyrans, benzofurans and spiro[4.5]decanes. Synth Commun 48: 2510–2521.
  • Aslan H, Akpınar DE, Oktemer A, Yakut M, Alagoz O (2014). Synthesis of Dihydropyrans and Dihydrofurans via Radical Cyclization of Unsaturated Alcohols and 1,3‐Dicarbonyl Compounds. Helvetica Chimica Acta 97: 652-663.
  • Bar G, Parsons AF, Thomas CB (2001). Manganese (III) acetate mediated radical reactions leading to araliopsine and related quinoline alkaloids. Tetrahedron 57: 4719–28.
  • Burgaz EV, Yilmaz M, Pekel T (2011). Radical cyclizations of conjugated esters and amides with 3-oxopropanenitriles mediated by manganese(III) acetate. ARKIVOC 363-376.
  • Curti C, Crozet MD, Vanelle P (2009). Microwave-assisted manganese(III) acetate based oxidative cyclizations of alkenes with b-ketosulfones. Tetrahedron 65: 200-5.
  • Eycken EV (2006). Microwave-assisted Synthesis of Heterocycles In: Eycken, E., Van derKappe, CO., eds. Springer: Berlin –Heidelberg.
  • Iqbal J, Bhetia B, Nayyar NK (1994). Transition metal-promoted free-radical reactions in organic synthesis: the formation of carbon-carbon bonds. Chem Rev 94: 519-64.
  • Kajikawa S, Nishino H, Kurosawa K (2001). Convenient Construction of Hexahydrobenzo[b]furan Skeleton Containing Heteroatoms. Choice of Mn(III)- and Ce(IV)-based Radical Cyclization. Heterocycles 54: 171-83.
  • Kappe CO, Dallinger D, Murphree SS (2009). Practical Microwave Synthesis for Organic Chemists – Strategies, Instruments, and Protocols. Wiley-VCH: Weinheim.
  • Kappe CO (2002). High-speed combinatorial synthesis utilizing microwave irradiation. Curr Opin Chem Biol 6: 314.
  • Kappe CO, Stadler A (2005). Microwaves in Organic and Medicinal Chemistry. Wiley-VCH: Weinheim.
  • Larhed M, Hallberg A (2001). Microwave-assisted high-speed chemistry: a new technique in drug discovery. Drug Discov Today 6: 406.
  • Larhed M, Moberg C, Hallberg A (2002). Microwave-Accelerated Homogeneous Catalysis in Organic Chemistry. Acc Chem Res 35: 717-727.
  • Li JJ (2013). Heterocyclic chemistry in drug discovery. John Wiley and Sons.
  • Mu XJ, Zou JP, Zeng RS, Wu JC (2005). Mn(III)-Promoted cyclization of substituted thioformanilides under microwave irradiation: a new reagent for 2-substituted benzothiazoles. Tetrahedron Lett 46: 4345.
  • Ozgur M, Yilmaz M, Nishino H, Avar EC, Dal H, Pekel AT, Hokelek T (2019). Efficient syntheses and antimicrobial activities of new thiophene containing pyranone and quinolinone derivatives using manganese(III) acetate: the effect of thiophene on ring closure–opening reactions. New J Chem 43: 5737-5751.
  • Pinna GA, Cignarella G, Ruiu S, Loriga G, Murineddu G, Villa S, Grella GE, Cossu G, Fratta W (2003). Synthesis of novel diazatricyclodecanes (DTDs). Effects of structural variation at the C3′ allyl end and at the phenyl ring of the cinnamyl chain on μ-receptor affinity and opioid antinociception. Bioorg Med Chem 11: 4015-4026.
  • Riddell FG (1980). The conformational analysis of heterocyclic compounds. Academic Press.
  • Wathey BTJ (2002). The impact of microwave-assisted organic chemistry on drug discovery. J Drug Discov Today 7: 373.
  • Yilmaz M, Yakut M, Pekel AT (2008). Synthesis of 2,3‐Dihydro‐4H‐furo[3,2‐c] chromen‐4‐ones and 2,3‐Dihydronaphtho[2,3‐b]furan‐4,9‐diones by the Radical Cyclizations of Hydroxyenones with Electron-Rich Alkenes using Manganese(III) Acetate. Synth Commun 38: 914–92.

Microwave assisted synthesis of ethyl 2,2-bis(4-fluorophenyl)-4-oxo-3,4- dihydro-2H-furo[3,2-c]chromene-3-carboxylate via manganese(III) acetate mediated radical cyclization reaction

Year 2020, Volume: 3 Issue: 2, 80 - 85, 31.10.2020

Abstract

“Ethyl 2,2-bis(4-fluorophenyl)-4-oxo-3,4-dihydro-2H-furo[3,2-c]chromene-3-carboxylate” is dihydro- furan-fused monocyclic heterocycles containing dihydrofurocoumarin framework. Compounds that include these core structures are especially important for drug discovery.
Manganese(III) acetate has been used as an efficient oxidizing agent for the preparation of “ethyl 2,2-bis(4-fluorophenyl)-4-oxo-3,4-dihydro-2H-furo[3,2-c]chromene-3-carboxylate” by the multi-steps reaction of ethyl 3,3-bis(4-fluorophenyl)acrylate and 4-hydroxycoumarin under microwave irradiation to perform faster heating times, significantly reduce reaction times, and the efficient solubilization of manganese(III) acetate in acetic acid. The cyclization reaction was achieved using reactivity of the carbonyl group within the molecule.

References

  • Akpınar DE, Ozgur M, Aslan H, Alagoz O, Oktemer A, Dal H, Hokelek T, Logoglu, E (2018). Synthesis, characterization, and investigations of antimicrobial activity of benzopyrans, benzofurans and spiro[4.5]decanes. Synth Commun 48: 2510–2521.
  • Aslan H, Akpınar DE, Oktemer A, Yakut M, Alagoz O (2014). Synthesis of Dihydropyrans and Dihydrofurans via Radical Cyclization of Unsaturated Alcohols and 1,3‐Dicarbonyl Compounds. Helvetica Chimica Acta 97: 652-663.
  • Bar G, Parsons AF, Thomas CB (2001). Manganese (III) acetate mediated radical reactions leading to araliopsine and related quinoline alkaloids. Tetrahedron 57: 4719–28.
  • Burgaz EV, Yilmaz M, Pekel T (2011). Radical cyclizations of conjugated esters and amides with 3-oxopropanenitriles mediated by manganese(III) acetate. ARKIVOC 363-376.
  • Curti C, Crozet MD, Vanelle P (2009). Microwave-assisted manganese(III) acetate based oxidative cyclizations of alkenes with b-ketosulfones. Tetrahedron 65: 200-5.
  • Eycken EV (2006). Microwave-assisted Synthesis of Heterocycles In: Eycken, E., Van derKappe, CO., eds. Springer: Berlin –Heidelberg.
  • Iqbal J, Bhetia B, Nayyar NK (1994). Transition metal-promoted free-radical reactions in organic synthesis: the formation of carbon-carbon bonds. Chem Rev 94: 519-64.
  • Kajikawa S, Nishino H, Kurosawa K (2001). Convenient Construction of Hexahydrobenzo[b]furan Skeleton Containing Heteroatoms. Choice of Mn(III)- and Ce(IV)-based Radical Cyclization. Heterocycles 54: 171-83.
  • Kappe CO, Dallinger D, Murphree SS (2009). Practical Microwave Synthesis for Organic Chemists – Strategies, Instruments, and Protocols. Wiley-VCH: Weinheim.
  • Kappe CO (2002). High-speed combinatorial synthesis utilizing microwave irradiation. Curr Opin Chem Biol 6: 314.
  • Kappe CO, Stadler A (2005). Microwaves in Organic and Medicinal Chemistry. Wiley-VCH: Weinheim.
  • Larhed M, Hallberg A (2001). Microwave-assisted high-speed chemistry: a new technique in drug discovery. Drug Discov Today 6: 406.
  • Larhed M, Moberg C, Hallberg A (2002). Microwave-Accelerated Homogeneous Catalysis in Organic Chemistry. Acc Chem Res 35: 717-727.
  • Li JJ (2013). Heterocyclic chemistry in drug discovery. John Wiley and Sons.
  • Mu XJ, Zou JP, Zeng RS, Wu JC (2005). Mn(III)-Promoted cyclization of substituted thioformanilides under microwave irradiation: a new reagent for 2-substituted benzothiazoles. Tetrahedron Lett 46: 4345.
  • Ozgur M, Yilmaz M, Nishino H, Avar EC, Dal H, Pekel AT, Hokelek T (2019). Efficient syntheses and antimicrobial activities of new thiophene containing pyranone and quinolinone derivatives using manganese(III) acetate: the effect of thiophene on ring closure–opening reactions. New J Chem 43: 5737-5751.
  • Pinna GA, Cignarella G, Ruiu S, Loriga G, Murineddu G, Villa S, Grella GE, Cossu G, Fratta W (2003). Synthesis of novel diazatricyclodecanes (DTDs). Effects of structural variation at the C3′ allyl end and at the phenyl ring of the cinnamyl chain on μ-receptor affinity and opioid antinociception. Bioorg Med Chem 11: 4015-4026.
  • Riddell FG (1980). The conformational analysis of heterocyclic compounds. Academic Press.
  • Wathey BTJ (2002). The impact of microwave-assisted organic chemistry on drug discovery. J Drug Discov Today 7: 373.
  • Yilmaz M, Yakut M, Pekel AT (2008). Synthesis of 2,3‐Dihydro‐4H‐furo[3,2‐c] chromen‐4‐ones and 2,3‐Dihydronaphtho[2,3‐b]furan‐4,9‐diones by the Radical Cyclizations of Hydroxyenones with Electron-Rich Alkenes using Manganese(III) Acetate. Synth Commun 38: 914–92.
There are 20 citations in total.

Details

Primary Language English
Subjects Organic Chemistry
Journal Section Research Article
Authors

Negar Khezri This is me

E. Vildan Burgaz

Publication Date October 31, 2020
Published in Issue Year 2020 Volume: 3 Issue: 2

Cite

APA Khezri, N., & Burgaz, E. V. (2020). Microwave assisted synthesis of ethyl 2,2-bis(4-fluorophenyl)-4-oxo-3,4- dihydro-2H-furo[3,2-c]chromene-3-carboxylate via manganese(III) acetate mediated radical cyclization reaction. EMU Journal of Pharmaceutical Sciences, 3(2), 80-85.
AMA Khezri N, Burgaz EV. Microwave assisted synthesis of ethyl 2,2-bis(4-fluorophenyl)-4-oxo-3,4- dihydro-2H-furo[3,2-c]chromene-3-carboxylate via manganese(III) acetate mediated radical cyclization reaction. EMUJPharmSci. October 2020;3(2):80-85.
Chicago Khezri, Negar, and E. Vildan Burgaz. “Microwave Assisted Synthesis of Ethyl 2,2-bis(4-Fluorophenyl)-4-Oxo-3,4- Dihydro-2H-furo[3,2-c]chromene-3-Carboxylate via manganese(III) Acetate Mediated Radical Cyclization Reaction”. EMU Journal of Pharmaceutical Sciences 3, no. 2 (October 2020): 80-85.
EndNote Khezri N, Burgaz EV (October 1, 2020) Microwave assisted synthesis of ethyl 2,2-bis(4-fluorophenyl)-4-oxo-3,4- dihydro-2H-furo[3,2-c]chromene-3-carboxylate via manganese(III) acetate mediated radical cyclization reaction. EMU Journal of Pharmaceutical Sciences 3 2 80–85.
IEEE N. Khezri and E. V. Burgaz, “Microwave assisted synthesis of ethyl 2,2-bis(4-fluorophenyl)-4-oxo-3,4- dihydro-2H-furo[3,2-c]chromene-3-carboxylate via manganese(III) acetate mediated radical cyclization reaction”, EMUJPharmSci, vol. 3, no. 2, pp. 80–85, 2020.
ISNAD Khezri, Negar - Burgaz, E. Vildan. “Microwave Assisted Synthesis of Ethyl 2,2-bis(4-Fluorophenyl)-4-Oxo-3,4- Dihydro-2H-furo[3,2-c]chromene-3-Carboxylate via manganese(III) Acetate Mediated Radical Cyclization Reaction”. EMU Journal of Pharmaceutical Sciences 3/2 (October 2020), 80-85.
JAMA Khezri N, Burgaz EV. Microwave assisted synthesis of ethyl 2,2-bis(4-fluorophenyl)-4-oxo-3,4- dihydro-2H-furo[3,2-c]chromene-3-carboxylate via manganese(III) acetate mediated radical cyclization reaction. EMUJPharmSci. 2020;3:80–85.
MLA Khezri, Negar and E. Vildan Burgaz. “Microwave Assisted Synthesis of Ethyl 2,2-bis(4-Fluorophenyl)-4-Oxo-3,4- Dihydro-2H-furo[3,2-c]chromene-3-Carboxylate via manganese(III) Acetate Mediated Radical Cyclization Reaction”. EMU Journal of Pharmaceutical Sciences, vol. 3, no. 2, 2020, pp. 80-85.
Vancouver Khezri N, Burgaz EV. Microwave assisted synthesis of ethyl 2,2-bis(4-fluorophenyl)-4-oxo-3,4- dihydro-2H-furo[3,2-c]chromene-3-carboxylate via manganese(III) acetate mediated radical cyclization reaction. EMUJPharmSci. 2020;3(2):80-5.