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Synthesis of Heteroaromatic Derivatives with Nitrogen Atoms: Tripyrrolyl Pyrimidine and Tripyrrolyl[1,3,5]triazine
Corresponding Author(s) : D.I. Jung
Asian Journal of Chemistry,
Vol. 25 No. 1 (2013): Vol 25 Issue 1
Abstract
As a part of a research program related to the synthetic study of pharmacologically and photoconductively interesting pyrrole derivatives, we have synthesized 1-arylpyrroles (3a-e), 9-arylcarbazoles (4a-e), aminophenylpyrroles (6a,b), dipyrrolylbenzenes (7a-c), 2,4,6-tri-pyrrol-1-yl-pyrimidine (8) and 2,4,6-tri-pyrrol-1-yl[1,3,5]triazine (9). We proposed a plausible mechanism for the formation of 9-arylcarbazole.
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- (a) B. Robinson, The Fischer Indole Synthesis; John Wiley and Sons: Chichester, (1982); (b) G.W. Gribble, J. Chem. Soc. Perkin Trans., 1045 (2000) and references cited therein; (c) G.R. Humphrey and J.T. Kucthe, Chem. Rer., 106, 2875 (2006); (d) B. Török, M. Abid and G. London, K.S. Angew. Chem., Int. Ed., 44, 3086 (2005).
- (a) M. Somei and F. Yamada, Nat. Prod. Rep., 21, 278 (2004); (b) A. Furstner, H. Szillat, B. Gabor and R. Mynott, J. Am. Chem. Soc., 120, 8305 (1998); (c) M. Somei and F. Yamada, Nat. Prod. Rep., 22, 73 (2005); (d) M. Török, M. Abid, S.C. Mhadgut and B. Török, Biochemistry, 45, 5377 (2006); (e) M. Abid and B. Török, Tetrahedron: Asymm., 16, 1547 (2005).
- (a) M.L. Hodges, M.L. Spera, M.W. Moody and W.D. Harman, J. Am. Chem. Soc., 118, 7117 (1996); (b) A.R. Katritzky, C.N. Fali and J. Li, J. Org. Chem., 62, 4148 (1997).
- (a) S.K. Bur and A. Padwa, Chem. Rev., 104, 2401 (2004); (b) T. Shimada, I. Nakamura and Y. Yamamoto, J. Am. Chem. Soc., 126, 10546 (2004); (c) Y. Ni-Shibayashi, M. Yoshikawa, Y. Inada, M.D. Milton, M. Hidai and S. Uemura, Angew. Chem. Int. Ed., 42, 2681 (2003); (d) D.J. Gorin, N.R. Davis and F.D. Toste, J. Am. Chem. Soc., 127, 11260 (2005); (e) O.V. Larionov and A. de Meijere, Angew. Chem. Int. Ed., 44, 5664 (2005); (f) Y. -Q. Fang and M. Lautens, Org. Lett., 7, 3549 (2005).
- C. Kashima, S. Hibi, T. Marugama and T. Omote, Tetrahedron Lett., 27, 2131 (1986).
- D.I. Jung, Y.Y. Kim, B.G. Yoo, Y.G. Lee and S.K. Choi, J. Korean Chem. Soc., 37, 982 (1993).
- D.I. Jung, Y.Y. Kim, B.G. Yoo, Y.G. Lee and S.K. Choi, Bull. Korean Chem. Soc., 15, 168 (2004).
- N. Elming and N. Clauson-Kass, Acta. Chem. Scand., 6, 867 (1952).
- Y. Chiang, R.L. Hinman, S. Teodoropulos and F.B. Wipple, Tetrahedron, 23, 745 (1967).
- A.D. Josey, Org. Syn. Coll., 5, 716 (1973).
- A. Mohammed, T. Liliana and T. Béla, Tetrahedron Lett., 48, 4047 (2007).
References
(a) B. Robinson, The Fischer Indole Synthesis; John Wiley and Sons: Chichester, (1982); (b) G.W. Gribble, J. Chem. Soc. Perkin Trans., 1045 (2000) and references cited therein; (c) G.R. Humphrey and J.T. Kucthe, Chem. Rer., 106, 2875 (2006); (d) B. Török, M. Abid and G. London, K.S. Angew. Chem., Int. Ed., 44, 3086 (2005).
(a) M. Somei and F. Yamada, Nat. Prod. Rep., 21, 278 (2004); (b) A. Furstner, H. Szillat, B. Gabor and R. Mynott, J. Am. Chem. Soc., 120, 8305 (1998); (c) M. Somei and F. Yamada, Nat. Prod. Rep., 22, 73 (2005); (d) M. Török, M. Abid, S.C. Mhadgut and B. Török, Biochemistry, 45, 5377 (2006); (e) M. Abid and B. Török, Tetrahedron: Asymm., 16, 1547 (2005).
(a) M.L. Hodges, M.L. Spera, M.W. Moody and W.D. Harman, J. Am. Chem. Soc., 118, 7117 (1996); (b) A.R. Katritzky, C.N. Fali and J. Li, J. Org. Chem., 62, 4148 (1997).
(a) S.K. Bur and A. Padwa, Chem. Rev., 104, 2401 (2004); (b) T. Shimada, I. Nakamura and Y. Yamamoto, J. Am. Chem. Soc., 126, 10546 (2004); (c) Y. Ni-Shibayashi, M. Yoshikawa, Y. Inada, M.D. Milton, M. Hidai and S. Uemura, Angew. Chem. Int. Ed., 42, 2681 (2003); (d) D.J. Gorin, N.R. Davis and F.D. Toste, J. Am. Chem. Soc., 127, 11260 (2005); (e) O.V. Larionov and A. de Meijere, Angew. Chem. Int. Ed., 44, 5664 (2005); (f) Y. -Q. Fang and M. Lautens, Org. Lett., 7, 3549 (2005).
C. Kashima, S. Hibi, T. Marugama and T. Omote, Tetrahedron Lett., 27, 2131 (1986).
D.I. Jung, Y.Y. Kim, B.G. Yoo, Y.G. Lee and S.K. Choi, J. Korean Chem. Soc., 37, 982 (1993).
D.I. Jung, Y.Y. Kim, B.G. Yoo, Y.G. Lee and S.K. Choi, Bull. Korean Chem. Soc., 15, 168 (2004).
N. Elming and N. Clauson-Kass, Acta. Chem. Scand., 6, 867 (1952).
Y. Chiang, R.L. Hinman, S. Teodoropulos and F.B. Wipple, Tetrahedron, 23, 745 (1967).
A.D. Josey, Org. Syn. Coll., 5, 716 (1973).
A. Mohammed, T. Liliana and T. Béla, Tetrahedron Lett., 48, 4047 (2007).