Asian Journal of Research in Chemistry

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A novel and eco-friendly method for Synthesis of 3-benzylidene-2-phenyl chroman-4-one analogs


Affiliations
1 Research Scholar, Department of Pharmaceutical Chemistry, A.R College of Pharmacy and G. H Patel Institute of Pharmacy, Vallabh Vidhyanagar, Anand, Gujarat, India., India
2 Professor, Department of Pharmaceutical Chemistry, A.R College of Pharmacy and G.H Patel Institute of Pharmacy, Vallabh Vidhyanagar, Anand, Gujarat, India, India
     

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The main aim of present work was to develop eco-friendly and green method for synthesis of 3-benzylidene-2- phenylchroman-4-one derivatives. For the synthesis of 3-benzylidene-2-phenylchroman-4-one derivatives variety of acid and base catalyzed methods was performed. HCl gas and p-TSA proved ineffective as catalyst. Concentrated HCl in n-butanol was very less effective method. Upon taking base catalyst, by product was formed when taking NaOH as catalyst and very low yield obtained using piperidine as catalyst. To overcome this problem, novel and eco-friendly method was developed in which barium hydroxide used as a base catalyst. In presence of ethanol product yield drastically increased. Main benefit of this method is reaction carried out by gradual trituration and very less amount of solvent was required. By using this method, product obtained in very high yield with more purity.

Keywords

3-Benzylidene-2-phenylchroman-4-one derivatives, Barium hydroxide, Gradual trituration.
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  • Krishnamurthy, H.G, Bram Prokash and Sathyanarayana S. on the first pot general synthesis of noval 3- benzal-2,3-dihydro 4.H [1] benzopyran – 4-ones. Ind. J. Chem. 1989; 28B: 279-81.

  • Seikel M.K, M.J Lounbury and Wang. S. One pot synthesis of 3arylidene flavanone. J.org.chem. 1962; 27: 2952.

  • Shah, P.R, N.M shah. synthesis of 3-arylidene flavanone. Chem.Ber. 1964; 97:1453.

  • Chawla H.M, S.K Sharma. synthesis of 3- arylidene flavanone using alkaline medium. Heterocycles. 1987; 26: 1527.

  • Shima H. M. E. Ketabforoosh et al. Synthesis and Anti-Cancer Activity Evaluation of New Dimethoxylated Chalcone and Flavanone Analogs. Arch. Pharm. Chem. Life Sci. 2014; 347: 1–8.

  • Bhagyesh Baviskar, Sureshbhi Patel, Bhushan Baviskar, SS Khadabadi, Mahendra Shiradkar. Design and Synthesis of Some Novel Chalcones as Potent Antimicrobial Agent. Asian J.Research Chem. 2008; 1(2): 67-69.

  • Bhaskar S. Dawane, Baseer M Shaikh, Namdev T. Khandare, Gajanan G. Mandawad, Santosh S. Chobe, Shankaraiah G. Konda. Synthesis of Some Novel Substituted Pyrazole Based Chalcones and Their In-Vitro Antimicrobial Activity. Asian J. Research Chem. 2010; 3(1): 90-93.

  • H.V. Shahare, G.R. Pawar, S.S. Patil, P.D. Patil. Synthesis and Biological Evaluation of New Chalcone Analogs. Asian J.Research Chem. 2011; 4(2): 237-240.

  • Gopi C., Dhanaraju M. D. Synthesis, Characterization and AntiMicrobial Evaluation of Derivative of Chalcone. Asian J. Research Chem. 2011; 4(2): 181-182.

  • Gondu Eswara Rao, S.A. Rahaman, A. Prameela Rani, Ch. M.M. Prasada Rao. Synthesis, Characterization and Antimicrobial Activity of Novel Chalcones from 1-[4-(1H-imidazol-1-yl) Phenyl] Ethanone. Asian J. Research Chem. 2013; 6(7): 687-689.

  • Pushkar Pratap Singh, B. Jayalakshmi, N. Senthil Kumar.Synthesis, Characterization and Antimicrobial Evaluation of Some New Chalcones. Asian J. Research Chem. 2013; 6(12): 1133-1136.

  • Suha K. Al-Mosawi, Hanan A. Al-Hazam, Abbas F. Abbas. Synthesis, Characterization and Biological Study of Some Chalcones derived from Terphthaldehyde. Asian J. of Research Chem. 2019; 12(3): 153-156. DOI: 10.5958/09744150.2019.00031.2

  • M. Safavi et al. Halogenated flavanones as potential apoptosisinducing agents: Synthesis and biological activity evaluation.European Journal of Medicinal Chemistry. 2012; 58: 573-580.

  • Y. Murti and P. Mishra. Synthesis and Evaluation of Flavanones as Anticancer Agents. Indian Journal of Pharmaceutical Sciences. 2014; 76(2): 163-166.

  • Yeonjoong Y, Hwang SA and Yoon H. 1H and 13C NMR spectral assignments of 2-hydroxychalcones. Magn. Reson. Chem. 2013; 51: 364–370.

  • Cabrera M., Simoens M., Falchi G. and Lavaggi M.L. Synthetic chalcones, flavanones, and flavones as antitumoral agents: Biological evaluation and structure activity relationships.Bioorganic & Medicinal Chemistry. 2007; 15: 3356–3367.

  • Laxmi Lal Dangi, Mangal S. Dulawat, Parul Tiwari, Shiv Singh Dulawat. New substituted m-Phenoxy chalcones; their synthesis by microwave irradiation and antifungal activity. Asian J.Research Chem. 2013; 6(5): 461-463.

  • Albogami A.S., Karama U., Amousa A.A, Khan M., Al-Mazroa S.A and Alkhathlan A.Z. Simple and Efficient One Step Synthesis of Functionalized Flavanones and Chalcones. Orient. J. Chem.

  • ; 28(2): 619-626.

  • Sharma N and Joshi YC. Synthesis of substituted chalcones under solvent–free microwave irradiation conditions and their antimicrobial evaluation. International Journal of Pharmacy and Pharmaceutical Sciences. 2012; 4(4): 436-439.

  • Borse SL. PhD. Thesis. Microwave Assisted Synthesis of Substituted Flavonoids and Pharmacological Evaluation.” Shri Jagdish Prasad Jhabarmal Tibrewala University, 2010.

  • Thornton M.T. PhD. Thesis. Synthesis of flavonoids and flavonoid-based designed multiple ligands for hypertension. Deakin University January, 2013, 32-33.

  • K. Ishwar Bhat, Ranee Kumari, Abhishek kumar, Pankaj Kumar. Synthesis of Some Novel Flavanones and Evaluation of Antioxidant Activities. Research J. Pharm. and Tech. 2019; 12(5): 2141-2144 DOI: 10.5958/0974-360X.2019.00355.X

  • Pramod Kulkarni, Pradip Wagh and Pudukulathan Zubaidha. An Improved and Eco-Friendly Method for the Synthesis of Flavanone by the Cyclization of 2’-Hydroxy Chalcone using Methane Sulphonic Acid as Catalyst. Chemistry Journal. 2012; 2(3): 106-110.

  • Preet Anand and Baldev Singh. Synthesis and evaluation of novel carbamate-substituted flavanone derivatives as potent acetylcholinesterase inhibitors and anti-amnestic agents. Med Chem Res. 2013; 22: 1648–1659. doi 10.1007/s00044-012-0162-3.

  • Yuh-Meei Lin, Yasheen Zhou, Michael T. Flavin, Li-Ming Zhou, Weiguo Niea and Ching Chen. Chalcones and Flavonoids as AntiTuberculosis Agents”, Bioorganic & Medicinal Chemistry. 2002; 10: 2795–2802.

  • Yogesh Murti and Pradeep Mishra. Flavanone: A Versatile Heterocyclic Nucleus. International Journal of ChemTech Research. 2014; 6(5): 3160-3178.

  • Srinivasu V. N. Vuppalapati, Likai Xia, Naushad Edayadulla, Yong Rok Lee. Mild and Efficient One-Pot Synthesis of Diverse Flavanone Derivatives via an Organocatalyzed Mannich-Type Reaction. Synthesis. 2014; 46: 465–474.

  • Moorthy N.S.H.N, Singh R.J, Singh H.P, and Gupta S.D. Synthesis, Biological Evaluation and In Silico Metabolic and Toxicity Prediction of Some Flavanone Derivatives. Chem. Pharm. Bull. 2006; 54(10): 1384-1390.

  • S. Saravanamurugan, M. Palanichamy, Banumathi Arabindoo, V. Murugesan. Solvent free synthesis of chalcone and flavanone over zinc oxide supported metal oxide catalysts. Catalysis Communications. 2005; 6: 399-403.

  • Elzbieta Budzisz et al. Biological Evaluation of 3- Benzylidenechromanones and Their Spiropyrazolines-Based Analogues. Molecules. 2020; 25: 1613.

  • Lincy Joseph, Mathew George. Analgesic and Anti-Oxidant Activities of Certain (E)-3 Arylidene Flavanones Synthesized by One Pot Method. Asian Journal of Research in Chemistry. 2009;

  • (3): 318-321.


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  • A novel and eco-friendly method for Synthesis of 3-benzylidene-2-phenyl chroman-4-one analogs

Abstract Views: 80  |  PDF Views: 0

Authors

Nikunj Patadiya
Research Scholar, Department of Pharmaceutical Chemistry, A.R College of Pharmacy and G. H Patel Institute of Pharmacy, Vallabh Vidhyanagar, Anand, Gujarat, India., India
Vipul Vaghela
Professor, Department of Pharmaceutical Chemistry, A.R College of Pharmacy and G.H Patel Institute of Pharmacy, Vallabh Vidhyanagar, Anand, Gujarat, India, India

Abstract


The main aim of present work was to develop eco-friendly and green method for synthesis of 3-benzylidene-2- phenylchroman-4-one derivatives. For the synthesis of 3-benzylidene-2-phenylchroman-4-one derivatives variety of acid and base catalyzed methods was performed. HCl gas and p-TSA proved ineffective as catalyst. Concentrated HCl in n-butanol was very less effective method. Upon taking base catalyst, by product was formed when taking NaOH as catalyst and very low yield obtained using piperidine as catalyst. To overcome this problem, novel and eco-friendly method was developed in which barium hydroxide used as a base catalyst. In presence of ethanol product yield drastically increased. Main benefit of this method is reaction carried out by gradual trituration and very less amount of solvent was required. By using this method, product obtained in very high yield with more purity.

Keywords


3-Benzylidene-2-phenylchroman-4-one derivatives, Barium hydroxide, Gradual trituration.

References