Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

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

Research Article

Metal-Free Synthesis of Pyrimidinone Derivatives via Biginelli Reaction Using Aqueous NaICl2

Author(s): Navnath T. Hatvate, Shrikant M. Ghodse, Krishna N. Mundlod and Vikas N. Telvekar*

Volume 17, Issue 8, 2020

Page: [613 - 617] Pages: 5

DOI: 10.2174/1570178617666191126095808

Price: $65

Abstract

Metal-free synthesis of pyrimidinone (alky/aryl) via Biginelli reaction in the presence of aqueous sodium dichloroiodate (NaICl2) was studied under reflux conditions. Herein, we first time report the synthesis of the aliphatic Biginelli product by using aliphatic aldehyde, cyclopentane, and urea. Several aromatic and heteroaromatic aldehydes were studied for the confirmation of the wide applicability of aq. NaICl2 for the synthesis of corresponding Biginelli products. The obtained desired products provide good to excellent yield.

Keywords: Three-component, pyrimidinone, bignelli reaction, sodium iodine dichloride, aliphatic aldehyde, cyclopentane.

Graphical Abstract

[1]
Singh, V.; Sapehiyia, V.; Srivastava, V.; Kaur, S. Catalysis Comm; , 2006, p. 7571.
[2]
Kappe, C.O.; Fabian, W.M.; Semones, M.A. Tetrahedron, 1997, 53, 2803.
[http://dx.doi.org/10.1016/S0040-4020(97)00022-7]
[3]
Haggarty, S.J.; Mayer, T.U.; Miyamoto, D.T.; Fathi, R.; King, R.W.; Mitchison, T.J.; Schreiber, S.L. Chem. Biol., 2000, 7(4), 275-286.
[http://dx.doi.org/10.1016/S1074-5521(00)00101-0 PMID: 10780927]
[4]
Lou, S.; Dai, P.; Schaus, S.E. J. Org. Chem., 2007, 72(26), 9998-10008.
[http://dx.doi.org/10.1021/jo701777g] [PMID: 18047372]
[5]
Subbagh, H.I.; Abu-Zaid, S.M.; Mahran, M.A.; Badria, F.A.; Al-Obaid, A.M. J. Med. Chem., 2000, 43, 2915.
[http://dx.doi.org/10.1021/jm000038m] [PMID: 10956199]
[6]
Biginelli, P.; Gazz, P. Chim. Ital., 1983, 23, 360.
[7]
Lu, J.; Ma, H. Synlett, 2000, 1, 63.
[8]
Paraskar, A.S.; Dewkar, G.K.; Sudalai, A. Tetrahedron Lett., 2003, 44, 3305.
[http://dx.doi.org/10.1016/S0040-4039(03)00619-1]
[9]
Kumar, K.; Kasthuraiah, M.; Reddy, C.S.; Reddy, C.D. Tetrahedron Lett., 2001, 42, 7873.
[http://dx.doi.org/10.1016/S0040-4039(01)01603-3]
[10]
More, U.B. Asian J. Chem., 2012, 24, 1906.
[11]
Sun, C.L.; Shi, Z. J. Chem. Rev., 2014, 114, 9219.
[http://dx.doi.org/10.1021/cr400274j]
[12]
Reddy, C.V.; Mahesh, M.; Raju, P.V.K.; Babu, T.R.; Reddy, V.V.N. Tetrahedron Lett., 2002, 43, 2657.
[http://dx.doi.org/10.1016/S0040-4039(02)00280-0]
[13]
Ramalingana, K.; Vijayalaxmi, P.; Kaimal, T.N.B. Synlett, 2001, 6, 863.
[http://dx.doi.org/10.1055/s-2001-14587]
[14]
Ranu, B.C.; Hajra, A.; Jana, U. J. Org. Chem., 2000, 65(19), 6270-6272.
[http://dx.doi.org/10.1021/jo000711f] [PMID: 10987976]
[15]
Akbas, E.; Berber, I.; Akyazi, I.; Anil, B.; Yildiz, E. Lett. Org. Chem., 2011, 8, 663.
[http://dx.doi.org/10.2174/157017811799304287]
[16]
Wang, Y.; Yu, J.; Yang, H.; Miao, Z.; Chen, R. Lett. Org. Chem., 2011, 8, 264.
[http://dx.doi.org/10.2174/157017811795371386]
[17]
Sehout, I.; Boulcina, R.; Boumoud, B.; Berree, F.; Carboni, F.; Debache, A. Lett. Org. Chem., 2013, 10, 463.
[http://dx.doi.org/10.2174/15701786113109990014]
[18]
Lal, K.; Paliwal, L.J.; Bagade, M.B. Lett. Org. Chem., 2016, 13, 255.
[http://dx.doi.org/10.2174/1570178613666160224005811]
[19]
Hajipour, A.R.; Ghayeb, Y.; Sheikhan, N.; Ruoho, A.E. Synth. Commun., 2011, 41, 2226.
[http://dx.doi.org/10.1080/00397911.2010.501474]
[20]
Ali, A.; Saeede, A.; Eskandar, K.; Somayeh, O. J. Chem. Soc., 2015, 62, 968.
[21]
Rahmani, S.; Ali, A.; Eskandar, K. Catal. Commun., 2014, 56, 184.
[http://dx.doi.org/10.1016/j.catcom.2014.07.002]
[22]
Heirati, S.Z.D.; Shirini, F.; Shojaei, A.F. RSC Advances, 2016, 6, 670.
[23]
Hatvate, N.T.; Ghodse, S.M.; Telvekar, V.N. Synth. Commun., 2018, 48, 285.
[http://dx.doi.org/10.1080/00397911.2017.1398330]
[24]
Hatvate, N.T.; Takale, B.S.; Ghodse, S.M.; Telvekar, V.N. Tetrahedron Lett., 2018, 59, 3892.
[http://dx.doi.org/10.1016/j.tetlet.2018.09.034]
[25]
Ghodse, S.M.; Telvekar, V.N. Tetrahedron Lett., 2015, 56, 472.
[http://dx.doi.org/10.1016/j.tetlet.2014.11.140]
[26]
Bhagat, B.S.; Ghodse, S.M.; Telvekar, V.N. J. Chem. Sci., 2018, 130, 10.
[http://dx.doi.org/10.1007/s12039-017-1414-z]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy