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Synthesis of Tetrazolo[1,5-c]quinazolines via Ph3PAuOTf-Catalyzed Double Hydroamination of Terminal Alkynes
Corresponding Author(s) : Pediredla G.V.V. Lakshmi
Asian Journal of Chemistry,
Vol. 26 No. 10 (2014): Vol 26 Issue 10
Abstract
An efficient tandem process is developed by using Ph3PAuOTf-catalyzed double hydroamination of alkynes for the synthesis of new fused tetrazolo[1,5-c]quinazolines, with 2-(1H-tetrazol-5-yl)anilines and alkynes in DCE at 100 °C.
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- (a) For reviews on atom economy, see: R.A. Sheldon, Pure Appl. Chem., 72, 1233 (2000); doi:10.1351/pac200072071233.; (b) B.M. Trost, Science, 254, 1471 (1991); doi:10.1126/science.1962206.; (c) B.M. Trost, Angew. Chem. Int. Ed. Engl., 34, 259 (1995); doi:10.1002/anie.199502591.
- N.T. Patil, V.S. Shinde and B. Sridhar, Angew. Chem. Int. Ed., 52, 2251 (2013); doi:10.1002/anie.201208738.
- (a) T.E. Müller, K.C. Hultzsch, M. Yus, F. Foubelo and M. Tada, Chem. Rev., 108, 3795 (2008); doi:10.1021/cr0306788; (b) R. Severin and S. Doye, Chem. Soc. Rev., 36, 1407 (2007); doi:10.1039/b600981f; (c) F. Pohlki and S. Doye, Chem. Soc. Rev., 32, 104 (2003); doi:10.1039/b200386b; (d) F. Alonso, I.P. Beletskaya and M. Yus, Chem. Rev., 104, 3079 (2004); doi:10.1021/cr0201068; (e) M. Nobis and B. Drießen-Hölscher, Angew. Chem. Int. Ed., 40, 3983 (2001); doi:10.1002/1521-3773(20011105)40:21<3983::AID-ANIE3983>3.0.CO;2-8; (f) T.E. Müller and M. Beller, Chem. Rev., 98, 675 (1998); doi:10.1021/cr960433d; (g) For selected recent examples, see: H. Duan, S. Sengupta, J.L. Petersen, N.G. Akhmedov and X. Shi, J. Am. Chem. Soc., 131, 12100 (2009); doi:10.1021/ja9041093; (h) X.-Y. Liu and C.-M. Che, Org. Lett., 11, 4204 (2009); doi:10.1021/ol901443b; (i) X. Zeng, G.D. Frey, S. Kousar and G. Bertrand, Eur. J. Chem., 15, 3056 (2009); doi:10.1002/chem.200802626; (j) S.R. Beeren, S.L. Dabb and B.A. Messerle, J. Organomet. Chem., 694, 309 (2009); doi:10.1016/j.jorganchem.2008.10.038.; (k) J.M. Carney, P.J. Donoghue, W.M. Wuest, O. Wiest and P. Helquist, Org. Lett., 10, 3903 (2008); doi:10.1021/ol801458g.
- N.T. Patil, R.D. Kavthe and V.S. Shinde, Tetrahedron, 68, 8079 (2012); doi:10.1016/j.tet.2012.05.125.
- N.T. Patil, P.G.V.V. Lakshmi, B. Sridhar, S. Patra, M. Pal Bhadra and C.R. Patra, Eur. J. Org. Chem., 1790 (2012); doi:10.1002/ejoc.201101822.
- N.T. Patil, P.G.V.V. Lakshmi and V. Singh, Eur. J. Org. Chem., 4719 (2010); doi:10.1002/ejoc.201000389.
- L. Lang, B. Li, W. Liu, L. Jiang, Z. Xu and G. Yin, Chem. Commun., 46, 448 (2009); doi:10.1039/b912284b.
- B.V. Golomolzin and I.Y. Postovskii, Chem. Heterocycl. Compd., 6, 266 (1970); doi:10.1007/BF00475015.
References
(a) For reviews on atom economy, see: R.A. Sheldon, Pure Appl. Chem., 72, 1233 (2000); doi:10.1351/pac200072071233.; (b) B.M. Trost, Science, 254, 1471 (1991); doi:10.1126/science.1962206.; (c) B.M. Trost, Angew. Chem. Int. Ed. Engl., 34, 259 (1995); doi:10.1002/anie.199502591.
N.T. Patil, V.S. Shinde and B. Sridhar, Angew. Chem. Int. Ed., 52, 2251 (2013); doi:10.1002/anie.201208738.
(a) T.E. Müller, K.C. Hultzsch, M. Yus, F. Foubelo and M. Tada, Chem. Rev., 108, 3795 (2008); doi:10.1021/cr0306788; (b) R. Severin and S. Doye, Chem. Soc. Rev., 36, 1407 (2007); doi:10.1039/b600981f; (c) F. Pohlki and S. Doye, Chem. Soc. Rev., 32, 104 (2003); doi:10.1039/b200386b; (d) F. Alonso, I.P. Beletskaya and M. Yus, Chem. Rev., 104, 3079 (2004); doi:10.1021/cr0201068; (e) M. Nobis and B. Drießen-Hölscher, Angew. Chem. Int. Ed., 40, 3983 (2001); doi:10.1002/1521-3773(20011105)40:21<3983::AID-ANIE3983>3.0.CO;2-8; (f) T.E. Müller and M. Beller, Chem. Rev., 98, 675 (1998); doi:10.1021/cr960433d; (g) For selected recent examples, see: H. Duan, S. Sengupta, J.L. Petersen, N.G. Akhmedov and X. Shi, J. Am. Chem. Soc., 131, 12100 (2009); doi:10.1021/ja9041093; (h) X.-Y. Liu and C.-M. Che, Org. Lett., 11, 4204 (2009); doi:10.1021/ol901443b; (i) X. Zeng, G.D. Frey, S. Kousar and G. Bertrand, Eur. J. Chem., 15, 3056 (2009); doi:10.1002/chem.200802626; (j) S.R. Beeren, S.L. Dabb and B.A. Messerle, J. Organomet. Chem., 694, 309 (2009); doi:10.1016/j.jorganchem.2008.10.038.; (k) J.M. Carney, P.J. Donoghue, W.M. Wuest, O. Wiest and P. Helquist, Org. Lett., 10, 3903 (2008); doi:10.1021/ol801458g.
N.T. Patil, R.D. Kavthe and V.S. Shinde, Tetrahedron, 68, 8079 (2012); doi:10.1016/j.tet.2012.05.125.
N.T. Patil, P.G.V.V. Lakshmi, B. Sridhar, S. Patra, M. Pal Bhadra and C.R. Patra, Eur. J. Org. Chem., 1790 (2012); doi:10.1002/ejoc.201101822.
N.T. Patil, P.G.V.V. Lakshmi and V. Singh, Eur. J. Org. Chem., 4719 (2010); doi:10.1002/ejoc.201000389.
L. Lang, B. Li, W. Liu, L. Jiang, Z. Xu and G. Yin, Chem. Commun., 46, 448 (2009); doi:10.1039/b912284b.
B.V. Golomolzin and I.Y. Postovskii, Chem. Heterocycl. Compd., 6, 266 (1970); doi:10.1007/BF00475015.