A Review of Synthesis Methods of Chalcones, Flavonoids, and Coumarins

Dinka Mulugeta

doi:doi:10.11648/j.sjc.20221002.12

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A Review of Synthesis Methods of Chalcones, Flavonoids, and Coumarins

Dinka Mulugeta

Published in Science Journal of Chemistry (Volume 10, Issue 2)

Received: 3 March 2022 Accepted: 6 April 2022 Published: 20 April 2022

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Abstract

Chalcones are the primary building blocks for flavonoids and isoflavonoids production. Chalcones are a three-carbon, -unsaturated carbonyl system. Chalcones form when an aromatic aldehyde reacts with acetophenones in the presence of a catalyst. For the synthesis of these molecules, a variety of methods and approaches have been reported. The Aldol condensation and Claisen-Schmidt condensation reactions are the most commonly referenced synthetic protocols in the literature, but the Suzuki reaction, Witting reaction, and Photo-Fries rearrangement have also been employed as synthetic procedures within the chalcone framework. SOCl₂ natural phosphate, lithium nitrate, amino grafted zeolites, zinc oxide, water, K₂CO₃, PEG400, silica sulfuric acid, ZrCl₄, and ionic liquid are among the most commonly used catalysts in the synthesis of the chalcone framework.

Published in	Science Journal of Chemistry (Volume 10, Issue 2)
DOI	10.11648/j.sjc.20221002.12
Page(s)	41-52
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2022. Published by Science Publishing Group

Keywords

Chalcones, Aldol Condensation, Claisen-Schmidt Condensation, Suzuki Reaction, Witting Reaction, Photo-Fries Rearrangement

References

[1]	Nowakowska, Z. Eur. J. Med. Chem, 2007, 42, 125.
[2]	Avila, H.; Smania, E.; Monache, F.; Junior, A. Bioorg. Med. Chem., 2008, 16, 9790–9794.
[3]	Rajendra Prasad Y; Lakshmana Rao A; Rambabu R; Ravi Kumar P. Oriental J. Chem, 2007, 23, 927-937.
[4]	Srinivasa Rao M.; Kotesh J.; Narukulla R.; Duddeck H. Arkivoc, 2004, xiv, 96-102.
[5]	Calvino V.; Picallo M.; López-Peinado A. J.; Martín-Aranda R. M.; Durán-Valle C. J. Appl. Surf. Sci., 2006, 252, 6071-6074.
[6]	Konieczny, M. T.; Konieczny, W.; Sabisz, M.; Skladanowski, A.; Eur. J. Med. Chem, 2007, 42 (5), 729-733.
[7]	Petrov, O.; Ivanova, Y.; Gerova, M. Catal. Commun., 2008, 9 (2), 315-316.
[8]	Sebti, S. d.; Solhy, A.; Smahi, A.; Kossir, A.; Oumimoun, H. Catal. Commun., 2002, 3 (8), 335-339.
[9]	Perozo-Rondón, E.; Martín-Aranda, R. M.; Casal, B.; Durán-Valle, C. J.; Lau, W. N.; Zhang, X. F.; Yeung, K. L. Catal. Today, 2006, 114 (2–3), 183-187.
[10]	Comisar, C. M.; Savage, P. E. Green Chem., 2004, 6 (4), 227-231.
[11]	Zhang, Z.; Wang, Y. W. D. G. W. Chem. Lett., 2003, 32 (10), 966-967.
[12]	Tanemura, K.; Suzuki, T.; Nishida, Y.; Horaguchi, T. ChemInform, 2005, 36 (38).
[13]	Thirunarayanan G.; Vanangamudi G. Arkivoc, 2006, xii, 58-64.
[14]	Dong, F.; Jian, C.; Zhenghao, F.; Kai, G.; Zuliang, L. Catal. Commun., 2008, 9, 1924-1927.
[15]	Tanka, K.; Sugino, T. Green. Chem. 2001, 3 , 133-134.
[16]	Chimenti, F.; Fioravanti, R.; Bolasco, A.; Chimenti, P.; Secci, D.; Rossi,. Bioor. Med. Chem. 2010, 18, 1273-1279.
[17]	Chen, D-U.; Kuo, P-Y.; Yang, D-Y. Bioorg. Med. Chem. 2005, 15, 2665-2668.
[18]	Kumar, D.; Patel, G.; Mishra, B. G.; Varma, R. S. Tetrahedron. Lett. 2008, 15, 6974-6976.
[19]	Claisen, L.; Claparede, A. Ber Dtsch. Chem. Ges. 1881, 15, 349.
[20]	Schmidt, J. G. Ber Dtsch. Chem. Ges. 1880, 13, 2342.
[21]	Cabrera, M.; Simoens, M.; Falchi, G.; Lavaggi, M. L.; Piro, O. E.; Castellano, E. E.; Vidal, A.; Azqueta, A.; Monge, A.; de Cerain, A. L.; Sagrera, G.; Seoane, G.; Cerecettoa, H.; Gonzaleza, M. Bioorg. Med. Chem. 2007, 15, 3356-3367.
[22]	Lv, P-S.; Sun, J.; Luo, Y.; Yang, Y.; Zhu, H-L. Bioorg. Med. Chem. Lett. 2010, 20. 4657-4660.
[23]	Kantam, M. L.; Prakash, B. V.; Reddy, C. V. Synth. Commu. 2005, 35, 1971-1978.
[24]	Sipos, G. Y.; Sirokmán, F. Nature 1964, 202, 489.
[25]	Kim, E-J.; Ryu, H. W.; Curtis-Long, M. J.; Han, J.; Kim, J. Y.; Cho, J. K.; Kang, D.; Park, K. H. Bioorg. Med. Chem. Lett. 2010, 20, 4237-4239.
[26]	Corma, A.; Gercía, A. Chem. Rev. 2003, 103, 4307-4366.
[27]	Kumar, A.; Atanksha. J. Mol. Cat. A: Chemical. 2007, 247, 212-216.
[28]	Narender, T.; Reddy, K. P. Tetrahedron. Lett. 2007, 48, 3177-3180.
[29]	Siddiqui, Z. N.; Musthafa, T. N. M. Tetrahedron. Lett. 2011, 52, 4008-4013.
[30]	Clark, J. H. Acc. Chem. Res. 2002, 35, 791-797.
[31]	Rateb, N. M.; Zohdi, H. F. Synth. Commun. 2009. 39, 2789-2794.
[32]	Mohammed Rayees Ahmad a, *, V. Girija Sastry a, Nasreen Bano b, Syed Anwar 2016.
[33]	Solhy, A.; Tahir, R.; Sebti, S.; Skouta, R.; Bousmina, M.; Zahouily, M.; Larzek, M. Appl. Catal., A: General. 2010, 374, 189-193.
[34]	Wang, H.; Zeng, J. Can. J. Chem. 2009, 87, 1209-1212.
[35]	Hallett, J. P.; Welton, T. Chem. Rev. 2011, 111, 3508-
[36]	Shen, J.; Wang, H.; Liu, H.; Sun, Y.; Liu, Z. J. Mol. Catal. A: Chemical. 2008, 280, 24-28.
[37]	Qian, H.; Liu, D. Ind. Eng. Chem. Res. 2011, 50, 1146-1149.
[38]	Sarda, S. R.; Jadhav, W. N.; Tekale, S. U.; Jadhav, G. V.; Patil, B. R.; Gajanan S. Suryawanshi, G. S.; Pawar, R. P. Lett. Org. Chem. 2009, 6, 481-484.
[39]	Subahsh, C.; Jagir, S. S Ind. J. Chem. 2015, 54, 1350-1354.
[40]	Chang, C-P.; Huang, Y-L.; Hong, F-E. Tetrahedron. 2005, 61, 3835-3839.
[41]	Al-Masum, M.; Ng, E.; Wai, M. C. Tetrahedron. Lett. 2011, 52 1008-1010.
[42]	Kumar, A.; Sharma, S.; Tripathi, V. D.; Srivastava, S. Tetrahedron. 2010, 66, 9445-9449.
[43]	Jeon, J-H.; Yang, D-K.; Jun, J-G. Bull. Korean Chem. Soci. 2011, 32, 65-70.
[44]	Xu, C.; Chen, G.; Huang, X. Org. Prep. Proced. Int. 1995, 27, 559-561.
[45]	Dambacher, J.; Zhao, W.; El-Batta, A.; Anness, R.; Jiang, C.; Bergdahl, M. Tetrahedron. Lett. 2005, 46, 4473-4477.
[46]	Marais, J. P.; Ferreira, D.; Slade, D. Phytochem 2005, 66.
[47]	Chandrasekhar, S.; Vijeender, K.; Reddy, K. V. Tetrahedron. Lett. 2005, 46, 6991-6993.
[48]	Sagrera, G. J., & Seoane, G. A. J. Braz. Chem. Soc. 2005, 16, 851-856.
[49]	Jeong, H. J.; Ryu, Y. B.; Park, S. J.; Kim, J. H.; Kwon, H. J.; Kim, J. H. Bioorg. Med. Chem. 2009, 17, 6816-6823.
[50]	Mondal, R.; Gupta, A. D.; Mallik, A. K. Tetrahedron Lett. 2011, 52, 5020-5024.
[51]	Vogel, S.; Ohmayer, S.; Brunner, G.; Heilmann, J. Bioorg. Med. Chem., 2008, 16, 4286–4293.
[52]	Awasthi, S.; Mishra, N.; Kumar, B.; Sharma, M.; Bhattacharya, A.; Mishra, LC.; Bhasin, V. Med. Chem. Rese. 200918: 407-420.
[53]	Yadav, H.; Gupta, P.; Pawar, PS.; Singour, PK. Med. Chem. Rese. 2010, 19: 1-8.
[54]	Bag, S.; Ramar, S.; Degani, MS.. Med. Chem. Rese. 200918: 309-316.
[55]	Yayli, N.; Ucuncu, O.; Yasar, A.; Kucuk, M.; Akyuz, E.; Karaoglu, SA. Tur. J. Chem, 2006, 30, 505-514.

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Dinka Mulugeta. (2022). A Review of Synthesis Methods of Chalcones, Flavonoids, and Coumarins. Science Journal of Chemistry, 10(2), 41-52. https://doi.org/10.11648/j.sjc.20221002.12

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ACS Style

Dinka Mulugeta. A Review of Synthesis Methods of Chalcones, Flavonoids, and Coumarins. Sci. J. Chem. 2022, 10(2), 41-52. doi: 10.11648/j.sjc.20221002.12

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AMA Style

Dinka Mulugeta. A Review of Synthesis Methods of Chalcones, Flavonoids, and Coumarins. Sci J Chem. 2022;10(2):41-52. doi: 10.11648/j.sjc.20221002.12

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@article{10.11648/j.sjc.20221002.12,
  author = {Dinka Mulugeta},
  title = {A Review of Synthesis Methods of Chalcones, Flavonoids, and Coumarins},
  journal = {Science Journal of Chemistry},
  volume = {10},
  number = {2},
  pages = {41-52},
  doi = {10.11648/j.sjc.20221002.12},
  url = {https://doi.org/10.11648/j.sjc.20221002.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20221002.12},
  abstract = {Chalcones are the primary building blocks for flavonoids and isoflavonoids production. Chalcones are a three-carbon, -unsaturated carbonyl system. Chalcones form when an aromatic aldehyde reacts with acetophenones in the presence of a catalyst. For the synthesis of these molecules, a variety of methods and approaches have been reported. The Aldol condensation and Claisen-Schmidt condensation reactions are the most commonly referenced synthetic protocols in the literature, but the Suzuki reaction, Witting reaction, and Photo-Fries rearrangement have also been employed as synthetic procedures within the chalcone framework. SOCl2 natural phosphate, lithium nitrate, amino grafted zeolites, zinc oxide, water, K2CO3, PEG400, silica sulfuric acid, ZrCl4, and ionic liquid are among the most commonly used catalysts in the synthesis of the chalcone framework.},
 year = {2022}
}

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TY  - JOUR
T1  - A Review of Synthesis Methods of Chalcones, Flavonoids, and Coumarins
AU  - Dinka Mulugeta
Y1  - 2022/04/20
PY  - 2022
N1  - https://doi.org/10.11648/j.sjc.20221002.12
DO  - 10.11648/j.sjc.20221002.12
T2  - Science Journal of Chemistry
JF  - Science Journal of Chemistry
JO  - Science Journal of Chemistry
SP  - 41
EP  - 52
PB  - Science Publishing Group
SN  - 2330-099X
UR  - https://doi.org/10.11648/j.sjc.20221002.12
AB  - Chalcones are the primary building blocks for flavonoids and isoflavonoids production. Chalcones are a three-carbon, -unsaturated carbonyl system. Chalcones form when an aromatic aldehyde reacts with acetophenones in the presence of a catalyst. For the synthesis of these molecules, a variety of methods and approaches have been reported. The Aldol condensation and Claisen-Schmidt condensation reactions are the most commonly referenced synthetic protocols in the literature, but the Suzuki reaction, Witting reaction, and Photo-Fries rearrangement have also been employed as synthetic procedures within the chalcone framework. SOCl2 natural phosphate, lithium nitrate, amino grafted zeolites, zinc oxide, water, K2CO3, PEG400, silica sulfuric acid, ZrCl4, and ionic liquid are among the most commonly used catalysts in the synthesis of the chalcone framework.
VL  - 10
IS  - 2
ER  -

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Author Information

Dinka Mulugeta

Food Science and Nutrition Research Directorate, Ethiopian Institute of Agricultural Research, Addis Ababa, Ethiopia

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Dinka Mulugeta. (2022). A Review of Synthesis Methods of Chalcones, Flavonoids, and Coumarins. Science Journal of Chemistry, 10(2), 41-52. https://doi.org/10.11648/j.sjc.20221002.12

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ACS Style

Dinka Mulugeta. A Review of Synthesis Methods of Chalcones, Flavonoids, and Coumarins. Sci. J. Chem. 2022, 10(2), 41-52. doi: 10.11648/j.sjc.20221002.12

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AMA Style

Dinka Mulugeta. A Review of Synthesis Methods of Chalcones, Flavonoids, and Coumarins. Sci J Chem. 2022;10(2):41-52. doi: 10.11648/j.sjc.20221002.12

Copy | Download

@article{10.11648/j.sjc.20221002.12,
  author = {Dinka Mulugeta},
  title = {A Review of Synthesis Methods of Chalcones, Flavonoids, and Coumarins},
  journal = {Science Journal of Chemistry},
  volume = {10},
  number = {2},
  pages = {41-52},
  doi = {10.11648/j.sjc.20221002.12},
  url = {https://doi.org/10.11648/j.sjc.20221002.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20221002.12},
  abstract = {Chalcones are the primary building blocks for flavonoids and isoflavonoids production. Chalcones are a three-carbon, -unsaturated carbonyl system. Chalcones form when an aromatic aldehyde reacts with acetophenones in the presence of a catalyst. For the synthesis of these molecules, a variety of methods and approaches have been reported. The Aldol condensation and Claisen-Schmidt condensation reactions are the most commonly referenced synthetic protocols in the literature, but the Suzuki reaction, Witting reaction, and Photo-Fries rearrangement have also been employed as synthetic procedures within the chalcone framework. SOCl2 natural phosphate, lithium nitrate, amino grafted zeolites, zinc oxide, water, K2CO3, PEG400, silica sulfuric acid, ZrCl4, and ionic liquid are among the most commonly used catalysts in the synthesis of the chalcone framework.},
 year = {2022}
}

Copy | Download

TY  - JOUR
T1  - A Review of Synthesis Methods of Chalcones, Flavonoids, and Coumarins
AU  - Dinka Mulugeta
Y1  - 2022/04/20
PY  - 2022
N1  - https://doi.org/10.11648/j.sjc.20221002.12
DO  - 10.11648/j.sjc.20221002.12
T2  - Science Journal of Chemistry
JF  - Science Journal of Chemistry
JO  - Science Journal of Chemistry
SP  - 41
EP  - 52
PB  - Science Publishing Group
SN  - 2330-099X
UR  - https://doi.org/10.11648/j.sjc.20221002.12
AB  - Chalcones are the primary building blocks for flavonoids and isoflavonoids production. Chalcones are a three-carbon, -unsaturated carbonyl system. Chalcones form when an aromatic aldehyde reacts with acetophenones in the presence of a catalyst. For the synthesis of these molecules, a variety of methods and approaches have been reported. The Aldol condensation and Claisen-Schmidt condensation reactions are the most commonly referenced synthetic protocols in the literature, but the Suzuki reaction, Witting reaction, and Photo-Fries rearrangement have also been employed as synthetic procedures within the chalcone framework. SOCl2 natural phosphate, lithium nitrate, amino grafted zeolites, zinc oxide, water, K2CO3, PEG400, silica sulfuric acid, ZrCl4, and ionic liquid are among the most commonly used catalysts in the synthesis of the chalcone framework.
VL  - 10
IS  - 2
ER  -

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