2,275
Views
8
CrossRef citations to date
0
Altmetric
RESEARCH LETTERS

Microwave-assisted practical and simple method for heterocyclization of o-phenylenediamine and aldehydes using DDQ as oxidant agent

&
Pages 129-133 | Received 31 Dec 2016, Accepted 29 Mar 2017, Published online: 18 Apr 2017

References

  • Denny, W.A.; Rewcastle, G.W.; Baguley, B.C. J. Med. Chem. 1990, 33, 814–819. doi: 10.1021/jm00164a054
  • (a) Porcari, A.R.; Devivar, R.V.; Kucera, L.S.; Drach, J.C.; Townsend, L.B. J. Med. Chem. 1998, 41, 1252–1262. (b) Roth, M.; Morningstar, M.L.; Boyer, P.L.; Hughes, S.H.; Buckheit, R.W., Michejda, C.J. J. Med. Chem. 1997, 40, 4199–4207. doi: 10.1021/jm970559i
  • Nakano, H.; Inoue, T.; Kawasaki, N.; Miyataka, H.; Matsumoto, H.; Taguchi, T.; Inagaki, N.; Nagai, H.; Satoh, T. Chem. Pharm. Bull. 1999, 47, 1573–1578. doi: 10.1248/cpb.47.1573
  • Fonseca, T.; Gigante, B.; Gilchrist, T.L. Tetrahedron. 2001, 57, 1793–1799. doi: 10.1016/S0040-4020(00)01158-3
  • Serafin, B.; Borkowska, G.; Główczyk, J.; Kowalska, I.; Rump, S. Polish J. Pharmacol. Pharm. 1989, 41, 89–96.
  • Kim, J.S.; Gatto, B.; Yu, C.; Liu, A.; Liu, L.F.; LaVoie, E. J. Med. Chem. 1996, 39, 992–998. doi: 10.1021/jm950412w
  • Kohara, Y.; Kubo, K.; Imamiya, E.; Wada, T.; Inada, Y.; Naka, T. J. Med. Chem. 1996, 39, 5228–5235. doi: 10.1021/jm960547h
  • Figge, A.; Altenbach, H.J.; Brauer, D.J.; Tielmann, P. Tetrahedron: Asymmetry. 2002, 13, 137–144. doi: 10.1016/S0957-4166(02)00079-4
  • (a) Bai, Y.; Lu, J.; Shi, Z.; Yang, B. Synlett. 2001, 4, 544–546. (b) Hasegawa, E.; Yoneoka, A.; Suzuki, K.; Kato, T.; Kitazume, T.; Yangi, K. Tetrahedron, 1999, 55, 12957–12968. doi: 10.1055/s-2001-12339
  • Lin, S.; Yang, L. Tetrahedron Lett. 2005, 46, 4315–4319. doi: 10.1016/j.tetlet.2005.04.101
  • Azizian, J.; Torabi, P.; Noei, J. Tetrahedron Lett. 2016, 57, 185–188. doi: 10.1016/j.tetlet.2015.11.092
  • Ghosh, P.; Subba, R. Tetrahedron Lett. 2015, 56, 2691–2694. doi: 10.1016/j.tetlet.2015.04.001
  • Sharghi, H.; Asemani, O.; Tabaei, S.M.H. J. Heterocycl. Chem. 2008, 45, 1293–1298. doi: 10.1002/jhet.5570450506
  • Marri, M.R.; Peraka, S.; Macharla, A.K.; Mameda, N.; Kodumuri, S.; Nama, N. Tetrahedron Lett. 2014, 55, 6520–6525. doi: 10.1016/j.tetlet.2014.09.081
  • Sun, Q.; Wang, C.J.; Gong, S.S.; Ai, Y.J.; Sun, H.B. Chin. Chem. Lett. 2015, 26, 297–300. doi: 10.1016/j.cclet.2014.11.014
  • Paudel, S.; Cao, Y.; Guo, S.; An, B.; Kim, K.M., Cheon, S.H. Bioorg. Med. Chem. 2015, 23, 6418–6426. doi: 10.1016/j.bmc.2015.08.022
  • Chaudhari, C.; Hakim Siddiki, S.M.A.; Shimizu, K.I. Tetrahedron Lett. 2015, 56, 4885–4888. doi: 10.1016/j.tetlet.2015.06.073
  • (a) Verner, E.; Katz, B.A.; Spencer, J.R.; Allen, D.; Hataye, J.; Hruzewicz, W.; Hui, H.C.; Kolesnikov, A.; Li, Y.; Luong, C.; Martelli, A.; Radika, K.; Rai, R.; She, M.; Shrader, W.; Sprengeler, P. A.; Trapp, S.; Wang, J.; Young, W.B.; Mackman, R.L. J. Med. Chem. 2001, 44, 2753–2771. (b) Kumar, S.; Kansal, V.; Bhaduri, A. Indian J. Chem. B, 1991, 20, 254–261. doi: 10.1021/jm0100638
  • Bhatnagar, I.; George, M.V. Tetrahedron. 1968, 24, 1293–1298. doi: 10.1016/0040-4020(68)88080-9
  • Bahrami, K.; Khodaei, M.M.; Kavianinia, I. Synthesis. 2007, 4, 547–550. doi: 10.1055/s-2007-965878
  • Patzold, F.; Zeuner, F.; Heyer, T.H.; Niclas, H. J. Synth. Commun. 1992, 22, 281–288. doi: 10.1080/00397919208021304
  • Eynde, J.J.V.; Delfosse, F.; Lor, P.; Harverbeke, Y.V. Tetrahedron. 1995, 51, 5813–5818. doi: 10.1016/0040-4020(95)00252-4
  • Kumar, R.; Joshi, Y.C. E-J. Chem. 2007, 4, 606–610. doi: 10.1155/2007/756267
  • (a) Weidner-Wells, M.A.; Ohemeng, K.A.; Nguyen, V.N.; Fraga-Spano, S.; Macielag, M.J.; Werblood, H.M.; Foleno, B.D.; Webb, G.C.; Barrett, J.F.; Hlasta, D.J. Bioorg. Med. Chem. Lett. 2001, 11, 1545–1548. (b) Austen, S.C.; Kane, J.M. J. Heterocycl. Chem. 2001, 38, 979–980. doi: 10.1016/S0960-894X(01)00024-5
  • Kumar, A.; Maurya, R.A.; Ahmad, P. J. Comb. Chem. 2009, 11, 198–201. doi: 10.1021/cc8001876
  • Mavandadi, F.; Lidström, P. Curr. Top. Med. Chem. 2004, 4, 773–792. doi: 10.2174/1568026043451078
  • (a) Kappe, C.O. Angew. Chem. Int. Ed. 2004, 43, 6250–6284. (b) Hayes, B. L. Aldrichim. Acta 2004, 37, 66–77. doi: 10.1002/anie.200400655
  • (a) De La Hoz, A.; Diaz-Ortiz, A.; Moreno, A. Chem. Soc. Rev. 2005, 34, 164–178. (b) Perreux, L.; Loupy, A. Tetrahedron. 2001, 57, 9199–9223. (c) Kuhnert, N. Angew. Chem. Int. Ed. 2002, 41, 1863–1866. (d) Strauss, C.R. Angew. Chem. Int. Ed. 2002, 41, 3589–3590. doi: 10.1039/B411438H
  • Naeimi, H.; Babaei, Z. J. Chin. Chem. Soc. 2015, 62, 41–46. doi: 10.1002/jccs.201400293
  • Bai, G.; Lan, X.; Liu, X.; Liu, C.; Shi, L.; Chen, Q.; Chen, G. Green Chem. 2014, 16, 3160–3168. doi: 10.1039/C3GC42551G
  • Jang, S.S.; Youn, S. W. Org. Biomol. Chem. 2016, 14, 2200–2204. doi: 10.1039/C6OB00074F
  • Bachhav, H.M.; Bagat, S.B.; Telvekar, V.N. Tetrahedron Lett. 2011, 52, 5697–5701. doi: 10.1016/j.tetlet.2011.08.105
  • Han, X.M.; Ma, H.Q.; Wang, Y.L. Arkivoc, 2007, 13, 150–154.
  • Navarrete-Vazquez, G.; Moreno-Diaz, H.; Aguirre-Crespo, F.; Leon-Rivera, I.; Villalobs-Molina, R.; Munoz-Munizd, O.; Estrada-Sotoa, S. Bioorg. Med. Chem. Lett. 2006, 16, 4169–4173. doi: 10.1016/j.bmcl.2006.05.082
  • Nagawade, R.R.; Shinde, D.B. Chin. Chem. Lett. 2006, 17, 453–456.
  • Chari, M.A.; Shobha, D.; Sasaki, T. Tetrahedron Lett. 2011, 52, 5575–5580. doi: 10.1016/j.tetlet.2011.08.047
  • Tavman, A.; Birteksoz, A.S.; Oksuzomer, F.S. Afr. J. Chem. 2012, 65, 150–158.
  • Behbahani, F.K.; Ziaei, P. Chem. Heterocycl. Compd. 2012, 48, 1011–1017. doi: 10.1007/s10593-012-1093-0