Abstract
A simple and appropriate procedure for the synthesis of quinazoline-2,4(1H,3H)-dione derivatives from isocyanides, aniline and isocyanate via the Cu-catalyzed intramolecular C-H activation reaction is reported. The advantages of this method are one-pot conditions, accessible starting materials- catalyst, high yield of products, and short reaction times. The structures are confirmed spectroscopically (1H- and 13C-NMR, IR and EI-MS) and by elemental analyses.
Keywords: C-H Activation, isocyanate, Cu-catalyzed, quinazoline-2, 4(1H, 3H)-diones, isocyanides, aniline.
Graphical Abstract
[http://dx.doi.org/10.1002/j.1552-4604.1980.tb01720.x] [PMID: 7000855]
[http://dx.doi.org/10.2165/00003495-198733050-00004] [PMID: 3297621]
[http://dx.doi.org/10.1039/C5CS00342C] [PMID: 26177889]
[http://dx.doi.org/10.1021/ml100004r] [PMID: 24900180]
[http://dx.doi.org/10.1248/cpb.53.1236] [PMID: 16204976]
[http://dx.doi.org/10.1055/s-2003-40211]
(b) Shi, D.Q.; Dou, G.L.; Li, Z.Y.; Ni, S.N.; Li, X.Y.; Wang, X.S.; Wu, H.; Ji, S.J. Tetrahedron 2007, 63, 9764-9773.
[http://dx.doi.org/10.1016/j.tet.2007.07.011]
(c) Ramana, D.V.; Vinayak, B.; Dileepkumar, V.; Murty, U.; Chowhan, L.R.; Chandrasekharam, M. Adv., 2016, 6, 21789-21794.
(d) Stevens, M.Y.; Wieckowski, K.; Wu, P.; Sawant, R.T.; Odell, L.R. Org. Biomol. Chem., 2015, 13(7), 2044-2054.
[http://dx.doi.org/10.1039/C4OB02417F] [PMID: 25518892]
[http://dx.doi.org/10.2174/1570178615666180914114010]
(b) Nematpour, M.; Abedi, E.; Abedi, E.; Lotfi, M. Lett. Org. Chem., 2018, 15, 727.
[http://dx.doi.org/10.2174/1570178614666170810125505]
[http://dx.doi.org/10.1126/science.1114731] [PMID: 16601184 ]
(b) Alberico, D.; Scott, M.E.; Lautens, M. Chem. Rev. 2007, 107(1), 174-238.
[http://dx.doi.org/10.1021/cr0509760] [PMID: 17212475 ]
(c) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal 2003, 345, 1077.
[http://dx.doi.org/10.1002/adsc.200303094]
(d) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev., 2002, 102(5), 1731-1770.
[http://dx.doi.org/10.1021/cr0104330] [PMID: 11996548]
b Nematpour, M.; Rezaee, E.; Jahani, M.; Tabatabai, S.A. Ultrason Sonochem, 2019, 50, 1-5.
[http://dx.doi.org/10.1016/j.ultsonch.2018.08.001] [PMID: 30213458]
(c) Nematpour, M.; Rezaee, E.; Tabatabai, S.A.; Jahani, M. Tetrahedron Lett, 2018, 59, 2054.
[http://dx.doi.org/10.1016/j.tetlet.2018.04.038]