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

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

Journal Name: Letters in Organic Chemistry

Volume 17 , Issue 8 , 2020

Become EABM
Become Reviewer

Graphical Abstract:


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.

[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 & PermissionsPrintExport Cite as

Article Details

VOLUME: 17
ISSUE: 8
Year: 2020
Page: [613 - 617]
Pages: 5
DOI: 10.2174/1570178617666191126095808
Price: $65

Article Metrics

PDF: 23
HTML: 1