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Microwave assisted synthesis of some halosubstituted chalcones

Year 2015, Volume: 2 Issue: 1, 1 - 12, 28.01.2015

Abstract

An efficient microwave assisted synthesis of halosubstituted chalcones by the condensation of halosubstituted ketones and substituted aldehydes. These reactions were found to economically cheap in comparison with classical synthesis.

References

  • Varma RS. Solvent-free organic syntheses using supported reagents and microwave irradiation. Green Chemistry. 1999;1(1):43–55.
  • Zangade S, Shinde A, Nalwar Y, Vibhute Y. Microwave induced efficient, convenient, rapid synthesis of substituted 2-pyrazolines as potentially antimicrobial agent. European Chemical Bulletin. 2014;3:310–4.
  • Kumar D, Kumar NM, Akamatsu K, Kusaka E, Harada H, Ito T. Synthesis and biological evaluation of indolyl chalcones as antitumor agents. Bioorganic & Medicinal Chemistry Letters. 2010 Jul;20(13):3916–9.
  • Siddiqui ZN, Mohammed Musthafa TN, Ahmad A, Khan AU. Thermal solvent-free synthesis of novel pyrazolyl chalcones and pyrazolines as potential antimicrobial agents. Bioorganic & Medicinal Chemistry Letters. 2011 May;21(10):2860–5.
  • Ravichandran R, Rajendran M, Devapiriam D. Studies on Chalcone Derivatives Antioxidant and Stability Constant. J Chem Biol Phys Sci. 2013;3:2446–58.
  • Gupta S, Shivahare R, Korthikunta V, Singh R, Gupta S, Tadigoppula N. Synthesis and biological evaluation of chalcones as potential antileishmanial agents. European Journal of Medicinal Chemistry. 2014 Jun;81:359–66.
  • Piotrowska DG, Cieślak M, Królewska K, Wróblewski AE. Design, synthesis and cytotoxicity of a new series of isoxazolidines derived from substituted chalcones. European Journal of Medicinal Chemistry. 2011 Apr;46(4):1382–9.
  • Sharma V, Chaudhary A, Arora S, Saxena AK, Ishar MPS. β-Ionone derived chalcones as potent antiproliferative agents. European Journal of Medicinal Chemistry. 2013 Nov;69:310–5.
  • Nowakowska Z. A review of anti-infective and anti-inflammatory chalcones. European Journal of Medicinal Chemistry. 2007 Feb;42(2):125–37.
  • Zangade S, Jadhav J, Vibhute Y, Dawane B. Synthesis and antimicrobial activity of some new chalcones and flavones containing substituted naphthalene moiety. J Chem Pharm Res. 2010;2:310–4.
  • Nerya O, Musa R, Khatib S, Tamir S, Vaya J. Chalcones as potent tyrosinase inhibitors: the effect of hydroxyl positions and numbers. Phytochemistry. 2004 May;65(10):1389–95.
  • Neto Bandeira G, Augusto Gomes da Camara C, Martins de Moraes M, Barros R, Muhammad S, Akhtar Y. Insecticidal activity of Muntingia calabura extracts against larvae and pupae of diamondback, Plutella xylostella (Lepidoptera, Plutellidae). Journal of King Saud University - Science [Internet]. 2012 Sep [cited 2014 Sep 4]; Available from: http://linkinghub.elsevier.com/retrieve/pii/S1018364712000444
  • Prasad Y, Rao A, Rambabu R, Kumar P. Synthesis and biological evaluation of some novel chalcone derivatives. Oriental J Chem. 2007;23:39417.
  • Rao M, Kotesh J, Narukulla R, Duddeck H. Synthesis and spectroscopic characterization of some chromanochalcones and their dihydro derivatives. Arkivoc. 2004;XIV:96.
  • Calvino V, Picallo M, López-Peinado AJ, Martín-Aranda RM, Durán-Valle CJ. Ultrasound accelerated Claisen–Schmidt condensation: A green route to chalcones. Applied Surface Science. 2006 Jun;252(17):6071–4.
  • Eddarir S, Cotelle N, Bakkour Y, Rolando C. An efficient synthesis of chalcones based on the Suzuki reaction. Tetrahedron Letters. 2003 Jul;44(28):5359–63.
  • Petrov O, Ivanova Y, Gerova M. SOCl2/EtOH: Catalytic system for synthesis of chalcones. Catalysis Communications. 2008 Feb;9(2):315–6.
  • Sebti S, Solhy A, Smahi A, Kossir A, Oumimoun H. Dramatic activity enhancement of natural phosphate catalyst by lithium nitrate. An efficient synthesis of chalcones. Catalysis Communications. 2002 Aug;3(8):335–9.
  • Macquarrie DJ, Nazih R, Sebti S. KF/natural phosphate as an efficient catalyst for synthesis of 2′-hydroxychalcones and flavanones. Green Chemistry. 2002 Feb 18;4(1):56–9.
  • Dong F, Jian C, Zhenghao F, Kai G, Zuliang L. Synthesis of chalcones via Claisen–Schmidt condensation reaction catalyzed by acyclic acidic ionic liquids. Catalysis Communications. 2008 May;9(9):1924–7.
  • Dong F, Jian C, Zhenghao F, Kai G, Zuliang L. Synthesis of chalcones via Claisen–Schmidt condensation reaction catalyzed by acyclic acidic ionic liquids. Catalysis Communications. 2008 May;9(9):1924–7.
  • Comisar CM, Savage PE. Kinetics of crossed aldol condensations in high-temperature water. Green Chemistry. 2004;6(4):227.
  • Zhang Z, Dong Y-W, Wang G-W. Efficient and Clean Aldol Condensation Catalyzed by Sodium Carbonate in Water. Chemistry Letters. 2003;32(10):966–7.
  • Tanemura K, Suzuki T, Nishida Y, Horaguchi T. Aldol Condensation in Water Using Polyethylene Glycol 400. Chemistry Letters. 2005;34(4):576–7.
  • Thirunarayanan G, Vanangamudi G. Synthesis of some 4-bromo-1-naphthyl chalcones using silica sulfuric acid reagent under solvent free conditions. Arkivoc. 2006;XII:58–64.
  • Sarda S, Jadhav W, Bhusare S, Wasmatkar S, Dake S, Pawar R. Solvent free NaOH Al2O3 supported synthesis of 1,3-diaryl-2-propene-1-ones. Int J Chem Tech Res. 2009;2:265–9.
  • Hazarkhani H, Kumar P, Kondiram KS, Shafi Gadwal IM. Highly Selective Claisen–Schmidt Condensation Catalyzed by Silica Chloride Under Solvent-Free Reaction Conditions. Synthetic Communications. 2010 Aug 31;40(19):2887–96.
  • Shinde A, Zangade S, Chavan S, Vibhute Y. Microwave induced synthesis of bis Schiff bases from propane-1,3-diamine as promising antimicrobial analogs. Org Commun. 2014;7:60–7.
  • Zangade S, Mokle S, Chavan S, Vibhute Y. 2-Methoxyethanol as an alternative reaction solvent for the synthesis of 1,5-benzodiazepines under microwave irradiation. Orbital - Electron J Chem. 2011;3:144–9.
  • Shakil NA, Singh MK, Sathiyendiran M, Kumar J, Padaria JC. Microwave synthesis, characterization and bio-efficacy evaluation of novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives. European Journal of Medicinal Chemistry. 2013 Jan;59:120–31.

BAZI HALO-SÜBSTİTÜE KALKONLARIN MİKRODALGA YARDIMLI SENTEZİ

Year 2015, Volume: 2 Issue: 1, 1 - 12, 28.01.2015

Abstract

Halo-sübstitüe ketonlar ve sübstitüe aldehitlerin kondensasyonu ile etkili bir mikrodalga yardımlı halosübstitüe kalkonların sentezi bildirilmiştir. Bu tepkimeler klasik sentezle karşılaştırıldığında ekonomik olarak ucuz bulunmuştur.

References

  • Varma RS. Solvent-free organic syntheses using supported reagents and microwave irradiation. Green Chemistry. 1999;1(1):43–55.
  • Zangade S, Shinde A, Nalwar Y, Vibhute Y. Microwave induced efficient, convenient, rapid synthesis of substituted 2-pyrazolines as potentially antimicrobial agent. European Chemical Bulletin. 2014;3:310–4.
  • Kumar D, Kumar NM, Akamatsu K, Kusaka E, Harada H, Ito T. Synthesis and biological evaluation of indolyl chalcones as antitumor agents. Bioorganic & Medicinal Chemistry Letters. 2010 Jul;20(13):3916–9.
  • Siddiqui ZN, Mohammed Musthafa TN, Ahmad A, Khan AU. Thermal solvent-free synthesis of novel pyrazolyl chalcones and pyrazolines as potential antimicrobial agents. Bioorganic & Medicinal Chemistry Letters. 2011 May;21(10):2860–5.
  • Ravichandran R, Rajendran M, Devapiriam D. Studies on Chalcone Derivatives Antioxidant and Stability Constant. J Chem Biol Phys Sci. 2013;3:2446–58.
  • Gupta S, Shivahare R, Korthikunta V, Singh R, Gupta S, Tadigoppula N. Synthesis and biological evaluation of chalcones as potential antileishmanial agents. European Journal of Medicinal Chemistry. 2014 Jun;81:359–66.
  • Piotrowska DG, Cieślak M, Królewska K, Wróblewski AE. Design, synthesis and cytotoxicity of a new series of isoxazolidines derived from substituted chalcones. European Journal of Medicinal Chemistry. 2011 Apr;46(4):1382–9.
  • Sharma V, Chaudhary A, Arora S, Saxena AK, Ishar MPS. β-Ionone derived chalcones as potent antiproliferative agents. European Journal of Medicinal Chemistry. 2013 Nov;69:310–5.
  • Nowakowska Z. A review of anti-infective and anti-inflammatory chalcones. European Journal of Medicinal Chemistry. 2007 Feb;42(2):125–37.
  • Zangade S, Jadhav J, Vibhute Y, Dawane B. Synthesis and antimicrobial activity of some new chalcones and flavones containing substituted naphthalene moiety. J Chem Pharm Res. 2010;2:310–4.
  • Nerya O, Musa R, Khatib S, Tamir S, Vaya J. Chalcones as potent tyrosinase inhibitors: the effect of hydroxyl positions and numbers. Phytochemistry. 2004 May;65(10):1389–95.
  • Neto Bandeira G, Augusto Gomes da Camara C, Martins de Moraes M, Barros R, Muhammad S, Akhtar Y. Insecticidal activity of Muntingia calabura extracts against larvae and pupae of diamondback, Plutella xylostella (Lepidoptera, Plutellidae). Journal of King Saud University - Science [Internet]. 2012 Sep [cited 2014 Sep 4]; Available from: http://linkinghub.elsevier.com/retrieve/pii/S1018364712000444
  • Prasad Y, Rao A, Rambabu R, Kumar P. Synthesis and biological evaluation of some novel chalcone derivatives. Oriental J Chem. 2007;23:39417.
  • Rao M, Kotesh J, Narukulla R, Duddeck H. Synthesis and spectroscopic characterization of some chromanochalcones and their dihydro derivatives. Arkivoc. 2004;XIV:96.
  • Calvino V, Picallo M, López-Peinado AJ, Martín-Aranda RM, Durán-Valle CJ. Ultrasound accelerated Claisen–Schmidt condensation: A green route to chalcones. Applied Surface Science. 2006 Jun;252(17):6071–4.
  • Eddarir S, Cotelle N, Bakkour Y, Rolando C. An efficient synthesis of chalcones based on the Suzuki reaction. Tetrahedron Letters. 2003 Jul;44(28):5359–63.
  • Petrov O, Ivanova Y, Gerova M. SOCl2/EtOH: Catalytic system for synthesis of chalcones. Catalysis Communications. 2008 Feb;9(2):315–6.
  • Sebti S, Solhy A, Smahi A, Kossir A, Oumimoun H. Dramatic activity enhancement of natural phosphate catalyst by lithium nitrate. An efficient synthesis of chalcones. Catalysis Communications. 2002 Aug;3(8):335–9.
  • Macquarrie DJ, Nazih R, Sebti S. KF/natural phosphate as an efficient catalyst for synthesis of 2′-hydroxychalcones and flavanones. Green Chemistry. 2002 Feb 18;4(1):56–9.
  • Dong F, Jian C, Zhenghao F, Kai G, Zuliang L. Synthesis of chalcones via Claisen–Schmidt condensation reaction catalyzed by acyclic acidic ionic liquids. Catalysis Communications. 2008 May;9(9):1924–7.
  • Dong F, Jian C, Zhenghao F, Kai G, Zuliang L. Synthesis of chalcones via Claisen–Schmidt condensation reaction catalyzed by acyclic acidic ionic liquids. Catalysis Communications. 2008 May;9(9):1924–7.
  • Comisar CM, Savage PE. Kinetics of crossed aldol condensations in high-temperature water. Green Chemistry. 2004;6(4):227.
  • Zhang Z, Dong Y-W, Wang G-W. Efficient and Clean Aldol Condensation Catalyzed by Sodium Carbonate in Water. Chemistry Letters. 2003;32(10):966–7.
  • Tanemura K, Suzuki T, Nishida Y, Horaguchi T. Aldol Condensation in Water Using Polyethylene Glycol 400. Chemistry Letters. 2005;34(4):576–7.
  • Thirunarayanan G, Vanangamudi G. Synthesis of some 4-bromo-1-naphthyl chalcones using silica sulfuric acid reagent under solvent free conditions. Arkivoc. 2006;XII:58–64.
  • Sarda S, Jadhav W, Bhusare S, Wasmatkar S, Dake S, Pawar R. Solvent free NaOH Al2O3 supported synthesis of 1,3-diaryl-2-propene-1-ones. Int J Chem Tech Res. 2009;2:265–9.
  • Hazarkhani H, Kumar P, Kondiram KS, Shafi Gadwal IM. Highly Selective Claisen–Schmidt Condensation Catalyzed by Silica Chloride Under Solvent-Free Reaction Conditions. Synthetic Communications. 2010 Aug 31;40(19):2887–96.
  • Shinde A, Zangade S, Chavan S, Vibhute Y. Microwave induced synthesis of bis Schiff bases from propane-1,3-diamine as promising antimicrobial analogs. Org Commun. 2014;7:60–7.
  • Zangade S, Mokle S, Chavan S, Vibhute Y. 2-Methoxyethanol as an alternative reaction solvent for the synthesis of 1,5-benzodiazepines under microwave irradiation. Orbital - Electron J Chem. 2011;3:144–9.
  • Shakil NA, Singh MK, Sathiyendiran M, Kumar J, Padaria JC. Microwave synthesis, characterization and bio-efficacy evaluation of novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives. European Journal of Medicinal Chemistry. 2013 Jan;59:120–31.
There are 30 citations in total.

Details

Primary Language Turkish
Journal Section Articles
Authors

Abhijit Unchadkar

Sainath Zangade

Avinash Shinde

Madhav Deshpande This is me

Publication Date January 28, 2015
Submission Date June 22, 2014
Published in Issue Year 2015 Volume: 2 Issue: 1

Cite

Vancouver Unchadkar A, Zangade S, Shinde A, Deshpande M. BAZI HALO-SÜBSTİTÜE KALKONLARIN MİKRODALGA YARDIMLI SENTEZİ. JOTCSA. 2015;2(1):1-12.