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An Efficient Synthesis of Indolo[1,2-c]quinazolines
Corresponding Author(s) : Pediredla G.V.V. Lakshmi
Asian Journal of Chemistry,
Vol. 26 No. 10 (2014): Vol 26 Issue 10
Abstract
Gold(I)-catalyzed cascade reaction was developed for the synthesis of new fused indolo[1,2-c]quinazolines by using 2-(3-methyl-1H-indol-2-yl)aniline and alkynes. This reaction provides a variety of biologically important quinazolines from easily available starting materials.
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- (a) L. Zhou, D.S. Bohle, H.-F. Jiang and C.-J. Li, Synlett, 937 (2009); doi:10.1055/s-0028-1088194; (b) X.-Y. Liu and C.-M. Che, Angew. Chem. Int. Ed., 48, 2367 (2009); doi:10.1002/anie.200805383; (c) K. Gräbe, B. Zwafelink and S. Doye, Eur. J. Org. Chem., 2009, 5565 (2009); doi:10.1002/ejoc.200900515; (d) K. Alex, A. Tillack, N. Schwarz and M. Beller, Org. Lett., 10, 2377 (2008); doi:10.1021/ol800592s; (e) K. Alex, A. Tillack, N. Schwarz and M. Beller, Angew. Chem. Int. Ed., 47, 2304 (2008); doi:10.1002/anie.200703823; (f) X.-Y. Liu, P. Ding, J.-S. Huang and C.-M. Che, Org. Lett., 9, 2645 (2007); doi:10.1021/ol070814l; (g) L. Ackermann and A. Althammer, Synlett, 3125 (2006); doi:10.1055/s-2006-950440; (h) C. Cao, Y. Li, Y. Shi and A.L. Odom, Chem. Commun., 2002 (2004); doi:10.1039/b405620e; (i) B. Ramanathan, A.J. Keith, D. Armstrong and A.L. Odom, Org. Lett., 6, 2957 (2004); doi:10.1021/ol0489088; (j) H. Siebeneicher, I. Bytschkov and S. Doye, Angew. Chem. Int. Ed., 42, 3042 (2003); doi:10.1002/anie.200351345; (k) C. Cao, Y. Shi and A.L. Odom, Org. Lett., 4, 2853 (2002); doi:10.1021/ol0201052.
- (a) A.N. Cayley, K.A. Gallagher, C. Ménard-Moyon, J.P. Schmidt, L.J. Diorazio and R.J.K. Taylor, Synthesis, 3846 (2008); doi:10.1055/s-0028-1083214; (b) C. Zhang, C.K. De, R. Mal and D. Seidel, J. Am. Chem. Soc., 130, 416 (2008); doi:10.1021/ja077473r; (c) K.M. Shakhidoyatov, Z.U. Samarov, N.I. Mukarramov, M.G. Levkovich, N.D. Abdullaev, B. Tashkhodzhaev, Y. Barakat and B.A. Urakov, Chem. Nat. Compd., 43, 441 (2006); doi:10.1007/s10600-007-0157-3; (d) W.R. Bowman, M.R.J. Elsegood, T. Stein and G.W. Weaver, Org. Biomol. Chem., 5, 103 (2007); doi:10.1039/b614075k; (e) M. Decker, F. Krauth and J. Lehmann, Bioorg. Med. Chem., 14, 1966 (2006); doi:10.1016/j.bmc.2005.10.044; (f) D.R. Ijzendoorn, P.N.M. Botman and R.H. Blaauw, Org. Lett., 8, 239 (2006); doi:10.1021/ol052598r; (g) S. Rault, S. Jolivet-Fouchet, F. Fabis, P. Bovy and P. Ochsenbein, Heterocycles, 51, 1257 (1999); doi:10.3987/COM-98-8412; (h) S. Jolivet-Fouchet, F. Fabis, P. Bovy, P. Ochsenbein and S. Rault, Tetrahedron Lett., 39, 819 (1998); doi:10.1016/S0040-4039(97)10595-0; (i) M. Yamato and Y. Takeuchi, Chem. Pharm. Bull. (Tokyo), 30, 1036 (1982); doi:10.1248/cpb.30.1036; (j) For general reviews, see: S.B. Mhaske and N.P. Argade, Tetrahedron, 62, 9787 (2006); doi:10.1016/j.tet.2006.07.098; (k) L. Orfi, F. Waczek, J. Pato, I. Varga, B. Hegymegi-Barakonyi, R. Houghten and G. Ker, Curr. Med. Chem., 11, 2549 (2004); doi:10.2174/0929867043364423; (l) D.J. Connolly, D. Cusack, T.P. O’Sullivan and P.J. Guiry, Tetrahedron, 61, 10153 (2005); doi:10.1016/j.tet.2005.07.010; (m) J.P. Michael, Nat. Prod. Rep., 24, 223 (2007); doi:10.1039/b509528j; (n) J.P. Michael, Nat. Prod. Rep., 22, 627 (2005); doi:10.1039/b413750g; (o) J.P. Michael, Nat. Prod. Rep., 21, 650 (2004); doi:10.1039/b310691h.
- (a) N.T. Patil and Y. Yamamoto, in ed.: S. Ma, Handbook of Cyclization ReactionsWiley-VCH: Weinheim, Chap. 9 (2009); (b) Y. Yamamoto, I.D. Gridnev, N.T. Patil and T. Jin, Chem. Commun., 5075 (2009); doi:10.1039/b909978f; (c) N.T. Patil and Y. Yamamoto, Top. Organomet. Chem., 19, 91 (2006); doi:10.1007/3418_014; (d) I. Nakamura and Y. Yamamoto, Chem. Rev., 104, 2127 (2004); doi:10.1021/cr020095i; (e) G. Zeni and R.C. Larock, Chem. Rev., 104, 2285 (2004); doi:10.1021/cr020085h.
- (a) For general reviews on cascade processes, see: K.C. Nicolaou and J.S. Chen, Chem. Soc. Rev., 38, 2993 (2009); doi:10.1039/b903290h; (b) K.C. Nicolaou, D.J. Edmonds and P.G. Bulger, Angew. Chem. Int. Ed., 45, 7134 (2006); doi:10.1002/anie.200601872; (c) A. de Meijere, P. von Zezschwitz and S. Bräse, Acc. Chem. Res., 38, 413 (2005); doi:10.1021/ar980025r; (d) J.M. Lee, Y. Na, H. Han and S. Chang, Chem. Soc. Rev., 33, 302 (2004); doi:10.1039/b309033g; (e) A. Ajamian and J.L. Gleason, Angew. Chem. Int. Ed., 43, 3754 (2004); doi:10.1002/anie.200301727; (f) L.F. Tietze, Chem. Rev., 96, 115 (1996); doi:10.1021/cr950027e.
- G. Liu, Y. Zhou, D. Lin, J. Wang, L. Zhang, H. Jiang and H. Liu, ACS Comb. Sci., 13, 209 (2011); doi:10.1021/co1000844.
- N.T. Patil, P.G.V.V. Lakshmi and V. Singh, Eur. J. Org. Chem., 2010, 4719 (2010); doi:10.1002/ejoc.201000389.
- B. Robinson and M.U. Zubair, Tetrahedron, 29, 1429 (1973); doi:10.1016/S0040-4020(01)83166-5.
References
(a) L. Zhou, D.S. Bohle, H.-F. Jiang and C.-J. Li, Synlett, 937 (2009); doi:10.1055/s-0028-1088194; (b) X.-Y. Liu and C.-M. Che, Angew. Chem. Int. Ed., 48, 2367 (2009); doi:10.1002/anie.200805383; (c) K. Gräbe, B. Zwafelink and S. Doye, Eur. J. Org. Chem., 2009, 5565 (2009); doi:10.1002/ejoc.200900515; (d) K. Alex, A. Tillack, N. Schwarz and M. Beller, Org. Lett., 10, 2377 (2008); doi:10.1021/ol800592s; (e) K. Alex, A. Tillack, N. Schwarz and M. Beller, Angew. Chem. Int. Ed., 47, 2304 (2008); doi:10.1002/anie.200703823; (f) X.-Y. Liu, P. Ding, J.-S. Huang and C.-M. Che, Org. Lett., 9, 2645 (2007); doi:10.1021/ol070814l; (g) L. Ackermann and A. Althammer, Synlett, 3125 (2006); doi:10.1055/s-2006-950440; (h) C. Cao, Y. Li, Y. Shi and A.L. Odom, Chem. Commun., 2002 (2004); doi:10.1039/b405620e; (i) B. Ramanathan, A.J. Keith, D. Armstrong and A.L. Odom, Org. Lett., 6, 2957 (2004); doi:10.1021/ol0489088; (j) H. Siebeneicher, I. Bytschkov and S. Doye, Angew. Chem. Int. Ed., 42, 3042 (2003); doi:10.1002/anie.200351345; (k) C. Cao, Y. Shi and A.L. Odom, Org. Lett., 4, 2853 (2002); doi:10.1021/ol0201052.
(a) A.N. Cayley, K.A. Gallagher, C. Ménard-Moyon, J.P. Schmidt, L.J. Diorazio and R.J.K. Taylor, Synthesis, 3846 (2008); doi:10.1055/s-0028-1083214; (b) C. Zhang, C.K. De, R. Mal and D. Seidel, J. Am. Chem. Soc., 130, 416 (2008); doi:10.1021/ja077473r; (c) K.M. Shakhidoyatov, Z.U. Samarov, N.I. Mukarramov, M.G. Levkovich, N.D. Abdullaev, B. Tashkhodzhaev, Y. Barakat and B.A. Urakov, Chem. Nat. Compd., 43, 441 (2006); doi:10.1007/s10600-007-0157-3; (d) W.R. Bowman, M.R.J. Elsegood, T. Stein and G.W. Weaver, Org. Biomol. Chem., 5, 103 (2007); doi:10.1039/b614075k; (e) M. Decker, F. Krauth and J. Lehmann, Bioorg. Med. Chem., 14, 1966 (2006); doi:10.1016/j.bmc.2005.10.044; (f) D.R. Ijzendoorn, P.N.M. Botman and R.H. Blaauw, Org. Lett., 8, 239 (2006); doi:10.1021/ol052598r; (g) S. Rault, S. Jolivet-Fouchet, F. Fabis, P. Bovy and P. Ochsenbein, Heterocycles, 51, 1257 (1999); doi:10.3987/COM-98-8412; (h) S. Jolivet-Fouchet, F. Fabis, P. Bovy, P. Ochsenbein and S. Rault, Tetrahedron Lett., 39, 819 (1998); doi:10.1016/S0040-4039(97)10595-0; (i) M. Yamato and Y. Takeuchi, Chem. Pharm. Bull. (Tokyo), 30, 1036 (1982); doi:10.1248/cpb.30.1036; (j) For general reviews, see: S.B. Mhaske and N.P. Argade, Tetrahedron, 62, 9787 (2006); doi:10.1016/j.tet.2006.07.098; (k) L. Orfi, F. Waczek, J. Pato, I. Varga, B. Hegymegi-Barakonyi, R. Houghten and G. Ker, Curr. Med. Chem., 11, 2549 (2004); doi:10.2174/0929867043364423; (l) D.J. Connolly, D. Cusack, T.P. O’Sullivan and P.J. Guiry, Tetrahedron, 61, 10153 (2005); doi:10.1016/j.tet.2005.07.010; (m) J.P. Michael, Nat. Prod. Rep., 24, 223 (2007); doi:10.1039/b509528j; (n) J.P. Michael, Nat. Prod. Rep., 22, 627 (2005); doi:10.1039/b413750g; (o) J.P. Michael, Nat. Prod. Rep., 21, 650 (2004); doi:10.1039/b310691h.
(a) N.T. Patil and Y. Yamamoto, in ed.: S. Ma, Handbook of Cyclization ReactionsWiley-VCH: Weinheim, Chap. 9 (2009); (b) Y. Yamamoto, I.D. Gridnev, N.T. Patil and T. Jin, Chem. Commun., 5075 (2009); doi:10.1039/b909978f; (c) N.T. Patil and Y. Yamamoto, Top. Organomet. Chem., 19, 91 (2006); doi:10.1007/3418_014; (d) I. Nakamura and Y. Yamamoto, Chem. Rev., 104, 2127 (2004); doi:10.1021/cr020095i; (e) G. Zeni and R.C. Larock, Chem. Rev., 104, 2285 (2004); doi:10.1021/cr020085h.
(a) For general reviews on cascade processes, see: K.C. Nicolaou and J.S. Chen, Chem. Soc. Rev., 38, 2993 (2009); doi:10.1039/b903290h; (b) K.C. Nicolaou, D.J. Edmonds and P.G. Bulger, Angew. Chem. Int. Ed., 45, 7134 (2006); doi:10.1002/anie.200601872; (c) A. de Meijere, P. von Zezschwitz and S. Bräse, Acc. Chem. Res., 38, 413 (2005); doi:10.1021/ar980025r; (d) J.M. Lee, Y. Na, H. Han and S. Chang, Chem. Soc. Rev., 33, 302 (2004); doi:10.1039/b309033g; (e) A. Ajamian and J.L. Gleason, Angew. Chem. Int. Ed., 43, 3754 (2004); doi:10.1002/anie.200301727; (f) L.F. Tietze, Chem. Rev., 96, 115 (1996); doi:10.1021/cr950027e.
G. Liu, Y. Zhou, D. Lin, J. Wang, L. Zhang, H. Jiang and H. Liu, ACS Comb. Sci., 13, 209 (2011); doi:10.1021/co1000844.
N.T. Patil, P.G.V.V. Lakshmi and V. Singh, Eur. J. Org. Chem., 2010, 4719 (2010); doi:10.1002/ejoc.201000389.
B. Robinson and M.U. Zubair, Tetrahedron, 29, 1429 (1973); doi:10.1016/S0040-4020(01)83166-5.