Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Review Article

Advances in the Arena of 1-(4-hydroxy-6-Methyl-2H-Pyran-2-On-3-yl)- 3-Arylpropenone: Preparation, Reactivity and Transformations

Author(s): Vishwas Chaudhri, Richa Prakash and Rashmi Pundeer*

Volume 19, Issue 2, 2022

Published on: 24 June, 2021

Page: [93 - 110] Pages: 18

DOI: 10.2174/1570178618666210624120204

Price: $65

Abstract

The 1-(4-hydroxy-6-methyl-2H-pyran-2-on-3-yl)-3-aryl-2-propenones, chalcone analogs derived from dehydroacetic acid (DHA), play a significant role in synthetic organic chemistry and proved to be an important intermediate for the wealth of multifarious biologically active molecules especially heterocyclic compounds. The review is an attempt to compile the transformations of DHA-chalcones to various classes of products.

Keywords: Chalcone, dehydroacetic acid, entrione, heterocycles, metal complexes, rearrangement.

« Previous Next »
Graphical Abstract

[1]
Rivera, C.; Pinero, E.; Giral, F. Experientia, 1976, 32, 1490.
[http://dx.doi.org/10.1007/BF01924409]
[2]
Nair, M.S.R.; Carey, S.T. Mycologia, 1979, 71(5), 1089-1096.
[http://dx.doi.org/10.1080/00275514.1979.12021118] [PMID: 545138]
[3]
Arndt, F.; Nachtwey, P. Ber. Dtsch. Chem. Ges., 1924, 57B, 1489-1491.
[http://dx.doi.org/10.1002/cber.19240570852]
[4]
Steele, A.B.; Boese, A.B.; Dull, M.F. J. Org. Chem., 1949, 14, 460-469.
[http://dx.doi.org/10.1021/jo01155a018]
[5]
Kaushal, R. J. Indian Chem. Soc., 1946, 23, 16.
[6]
Pechmann, H.V.; Baltzer, O. Ber. Dtsch. Chem. Ges., 1891, 24, 3144-3153.
[http://dx.doi.org/10.1002/cber.189102402155]
[7]
Fiest, F. Liebigs Ann., 1890, 257, 253-297.
[http://dx.doi.org/10.1002/jlac.18902570302]
[8]
(a) Turpin, G.S. J. Chem. Soc., 1891, 59, 179-189.
(b) Collie, J.N.; Hilditch, T.P. J. Chem. Soc., 1907, 91, 787.
[http://dx.doi.org/10.1039/CT9079100787]
[9]
Rassweiler, C.F.; Adams, R. J. Am. Chem. Soc., 1924, 46, 2758-2764.
[http://dx.doi.org/10.1021/ja01677a022]
[10]
Prakash, O.; Kumar, A.; Singh, S.P. Heterocycles, 2004, 63, 1193-1220.
[http://dx.doi.org/10.3987/REV-03-572]
[11]
Aggarwal, R.; Walia, S.; Rani, C. Heterocycles, 2017, 94, 1197-1244.
[http://dx.doi.org/10.3987/REV-17-860]
[12]
Kumar, D.; Singh, S.P. J. Indian Chem. Soc., 2006, 83, 419-426.
[13]
Gupta, G.K.; Mittal, A.; Kumar, V. Lett. Org. Chem., 2014, 11, 273-286.
[http://dx.doi.org/10.2174/1570178610666131230235759]
[14]
Fadda, A.A.; Elattar, K.M. Synth. Commun., 2015, 46, 1-30.
[http://dx.doi.org/10.1080/00397911.2015.1092549]
[15]
Penta, S. Dehydroacetic acid and its derivatives: Useful Synthons in Organic Synthesis. Ed; Elsevier, 2017.
[16]
Wiley, R.H.; Jarboe, C.H.; Ellert, H.G. J. Am. Chem. Soc., 1955, 77, 5102-5107.
[http://dx.doi.org/10.1021/ja01624a045]
[17]
Vul’fson, N.S.; Savenkova, E.V.; Senyavina, L.B. Zh. Obshch. Khim., 1964, 34, 2743-2747.
[18]
Vul’fson, N.S.; Savenkova, E.V.; Senyavina, L.B. Bull. Acad. Sci. USSR, Div. Chem. Sci., 1966, 15, 1541-1545.
[http://dx.doi.org/10.1007/BF00848912]
[19]
Rehse, K.; Rüther, D.; Einflu, B. Arch. Pharm. (Weinheim), 1984, 317(3), 262-267.
[http://dx.doi.org/10.1002/ardp.19843170313] [PMID: 6732447]
[20]
Siddiqui, Z.N.; Praveen, S.; Mohammed, M.T.N. Indian J. Chem., 2011, 50B, 910-917.
[21]
Siddiqui, Z.N.; Khan, T. J. Braz. Chem. Soc., 2014, 25(6), 1002-1011.
[22]
Thabti, S.; Djedouani, A.; Rahmouni, S.; Touzani, R.; Bendaas, A.; Mousser, A. J. Mol. Struct., 2015, 1102, 295-301.
[http://dx.doi.org/10.1016/j.molstruc.2015.08.071]
[23]
Sundar, P.S.; Gunasheela, D. Eur. J. Pharm. Med. Res., 2016, 3(7), 381-384.
[24]
Motegaonkar, M.B.; Salunke, S.D. Pharma Chem., 2017, 9(9), 118-121.
[25]
Lal, K.; Yadav, P.; Kumar, A.; Kumar, A.; Paul, A.K. Bioorg. Chem., 2018, 77, 236-244.
[http://dx.doi.org/10.1016/j.bioorg.2018.01.016] [PMID: 29421698]
[26]
Teimuri-Mofrad, R.; Rahimpour, K.; Gholizadeh, M.J. Iran. Chem. Soc., 2019, 17, 1103-1109.
[http://dx.doi.org/10.1007/s13738-019-01839-4]
[27]
Baziz, N.A.; Rachedi, Y.; Chemat, F.; Hamdi, M. Asian J. Chem., 2008, 20, 2610-2622.
[28]
Prasad, Y.R.; Rajasekhar, K.K.; Rao, B.B.; Shankarananth, V.; Murthy, K. Int. J. Innovations Pharm. Res., 2010, 1, 44-47.
[29]
Prakash, O.; Kumar, A.; Kinger, M.; Singh, S.P. Indian J. Chem., 2006, 44B(2), 456-460.
[30]
Levai, A.; Jeko, J. Monatsh. Chem., 2006, 137, 339-345.
[http://dx.doi.org/10.1007/s00706-006-0437-9]
[31]
Siddiqui, Z.N.; Praveen, S.; Mohammed, M.T.N. Indian J. Chem., 2011, 50B, 910-917.
[32]
Kinger, M.; Gupta, V.D.; Singh, J.; Arora, A.K.; Jaswal, V.S. Asian J. Chem., 2014, 23, 8084-8086.
[http://dx.doi.org/10.14233/ajchem.2014.17145]
[33]
Motegaonkar, M.B.; Salunke, S.D. Int. J. Heterocycl. Chem., 2017, 7, 26-35.
[34]
Saji Redha, I.H.A.L-B.; Thamir, S.M. J. Sci., 2013, 24(3), 41-56.
[35]
Motegaokar, M.; Dhage, S.D. World J. Pharm. Pharm. Sci., 2018, 7(4), 814-821.
[36]
Rudenko, R.V.; Komykhov, S.A.; Musatov, V.I.; Desenko, S.M. J. Heterocycl. Chem., 2009, 46(2), 285-288.
[http://dx.doi.org/10.1002/jhet.81]
[37]
Kaur, N.; Aggarwal, A.K.; Sharma, N.; Choudhary, B. Int. J. Pharm. Sci. Drug Res., 2012, 4(3), 199-204.
[38]
Prakash, O.; Kumar, A.; Sadana, A.; Singh, S.P. Synthesis, 2006, 1, 21-23.
[http://dx.doi.org/10.1055/s-2005-921751]
[39]
Prakash, O.; Kumar, A.; Sadana, A.; Prakash, R.; Singh, S.; Claramunt, P.R.M.; Sanz, D.; Alkorta, I.; Elgeuero, J. Tetrahedron, 2005, 61, 6642-6651.
[http://dx.doi.org/10.1016/j.tet.2005.03.035]
[40]
Pinilla, E.; Torres, M.R.; Claramunt, R.M.; Sanz, D.; Prakash, R.; Singh, S.P.; Alkorta, I.; Elguero, J. ARKIVOC, 2006, ii, 136-142.
[http://dx.doi.org/10.3998/ark.5550190.0007.216]
[41]
Prakash, O.; Kumar, A.; Sadana, A.; Singh, S.P. Synth. Commun., 2002, 32(17), 2663-2667.
[http://dx.doi.org/10.1081/SCC-120006030]
[42]
Claramunt, R.M.; Sanz, D.; Aggarwal, S.; Kumar, A.; Prakash, O.; Singh, S.P.; Elguero, J. ARKIVOC, 2006, xiv, 35-45.
[http://dx.doi.org/10.3998/ark.5550190.0007.e06]
[43]
Briel, D.; Rudolph, I.; Unverferth, K.; Mann, S. Pharmazie, 2010, 65(9), 641-644.
[PMID: 21038839]
[44]
Hassan, M.A.; El-Kady, M.; El-Borai, M.; Abd El-Moaty, A.A.; Hassan, M.A.; El-Kady, M.; El-Borai, M.; Abd El-Moaty, A.A. Rev. Roum. Chim., 1985, 30, 245-248.
[45]
Grunwald, C.; Kronbach, C.; Egerland, U.; Schindler, R.; Dieckmann, R.; Heinecke, K.; Höfgen, N.; Unverferth, K. Pharmazie, 2011, 66(2), 98-104.
[http://dx.doi.org/10.1002/chin.201125210] [PMID: 21434570]
[46]
Muthukumara, M. J. Coord. Chem., 2010, 63, 1263.
[47]
Patange, V.N.; Arbat, B.R. J. Serb. Chem. Soc., 2011, 76, 1237.
[http://dx.doi.org/10.2298/JSC100531108P]
[48]
Tambov, K.V.; Voevodina, I.V.; Manaev, A.V.; Ivanenkov, Y.A.; Neamati, N.; Travena, V.F. Russ. Chem. Bull., 2012, 61, 78.
[http://dx.doi.org/10.1007/s11172-012-0012-y]
[49]
Thaker, B.T.; Barvalia, R.S. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2013, 112, 101-109.
[http://dx.doi.org/10.1016/j.saa.2013.03.002] [PMID: 23659957]
[50]
Dovbii, Y.M.; Chernii, V.Y.; Tretyakova, I.M.; Gorski, A.V.; Starukhin, A.S.; Volkov, S.V. Ukrain Chem. J., 2015, 81, 79.
[51]
Jawale, B.H.; Mane, Y.D.; Sarnikar, Y.P.; Khade, B.C.; Lonkar, S.M. World. J. Pharm. Res., 2017, 6, 1957.
[52]
Jawale, B.H.; Salunke, S.D. Res. J. Pharm. Biol. Chem. Sci., 2017, 8, 1260.
[53]
Jawale, B.H.; Salunke, S.D. J Chemical. Pharm. Sci., 2017, 10, 1028.
[54]
Tabti, S.; Benmahmoud, M.; Djedouani, A.; Semmari, L. J. Mater. Environ. Sci, 2018, 9, 2624.
[55]
Tabti, S.; Djedouani, A.; Aggoun, D.; Warad, I.; Rahmouni, S.; Romdhane, S.; Fouzi, H. J. Mol. Struct., 2018, 155, 11.
[http://dx.doi.org/10.1016/j.molstruc.2017.10.084]
[56]
Jawale, B.H. Int. J. Eng. Res. Technol. (Ahmedabad), 2019, 8, 803.
[57]
Hamdi, D.C.M.; Baboulhe, M.; Lattes, V.S.A. J. Heterocycl. Chem., 1986, 23, 1721-1724.
[http://dx.doi.org/10.1002/jhet.5570230624]
[58]
Kovalska, V.A.; Chernii, S.; Losytskyy, M.; Tretyakova, I.; Dovbii, Y.; Gorski, V.; Chernii, R.; Czerwieniec, S. New J. Chem., 2018, 42, 13308-13318.
[http://dx.doi.org/10.1039/C8NJ01020J]
[59]
Walker, G.N. J. Am. Chem. Soc., 1956, 78, 3201-3205.
[http://dx.doi.org/10.1021/ja01594a062]
[60]
Birch, J.; Cameron, D.W.; Rickards, R.W. J. Chem. Soc., 1960, 4395-4400.
[http://dx.doi.org/10.1039/JR9600004395]
[61]
Kataoka, M.; Ohno, M. CA (Edinb.), 1973, 80, 59864q.
[62]
Rachedi, Y.; Hamdi, V. Synth. Commun., 1989, 19(20), 3437-3442.
[http://dx.doi.org/10.1080/00397918908052752]
[63]
Baziz, N.A.; Rachedi, Y.; Silva, A.M.S. ARKIVOC, 2010, x, 86-97.
[http://dx.doi.org/10.3998/ark.5550190.0011.a08]
[64]
Pashkovsky, F.S.; Dontsu, J.S.; Rubinov, D.B. Chem. Heterocycl. Compd., 2015, 50(10), 1421-1431.
[http://dx.doi.org/10.1007/s10593-014-1606-0]
[65]
Baziz, N.; Hamdi, S.M.; Silva, A.M.S.; Rachedi, Y.; Hamdi, M.; Trarie, M.A. J. Heterocycl. Chem., 2014, 51, 1240-1245.
[http://dx.doi.org/10.1002/jhet.1694]
[66]
Takeuchi, N.; Nakagawa, H.; Tobinaga, S. Chem. Pharm. Bull. (Tokyo), 1980, 28, 3002-3006.
[http://dx.doi.org/10.1248/cpb.28.3002]

Rights & Permissions Print Cite
Article Metrics
20
1
© 2024 Bentham Science Publishers | Privacy Policy