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Volumn 3, Issue 6, 2005, Pages 996-1001

Synthesis of 2-pyridone-fused 2,2′-bipyridine derivatives. An unexpectedly complex solid state structure of 3,6-dimethyl-9H-4,5,9- triazaphenanthren-10-one

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBONS; COMPLEXATION; COORDINATION REACTIONS; CRYSTAL STRUCTURE; DIMERIZATION; HYDROGEN BONDS; MOLECULAR STRUCTURE; NITROGEN COMPOUNDS; PROTONS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION ANALYSIS;

EID: 16244378225     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b417485b     Document Type: Article
Times cited : (16)

References (58)
  • 2
    • 0000942477 scopus 로고    scopus 로고
    • S. C. Zimmerman and P. S. Corbin, Struct. Bonding (Berlin), 2000, 96, 63; J. A. R. Navarro and B. Lippert, Coord. Chem. Rev., 1999, 185-186, 653.
    • (1999) Coord. Chem. Rev. , vol.185-186 , pp. 653
    • Navarro, J.A.R.1    Lippert, B.2
  • 4
    • 2742517055 scopus 로고    scopus 로고
    • A. Gavezotti, Faraday Discuss., 1997, 106, 63; A. Gavezotti, Acc. Chem. Res., 1994, 27, 309.
    • (1997) Faraday Discuss. , vol.106 , pp. 63
    • Gavezotti, A.1
  • 5
    • 0001410276 scopus 로고
    • A. Gavezotti, Faraday Discuss., 1997, 106, 63; A. Gavezotti, Acc. Chem. Res., 1994, 27, 309.
    • (1994) Acc. Chem. Res. , vol.27 , pp. 309
    • Gavezotti, A.1
  • 8
    • 0010783816 scopus 로고    scopus 로고
    • and references therein
    • A. M. Beatty, CrystEngComm, 2001, 3, 243 and references therein.
    • (2001) Cryst Eng Comm , vol.3 , pp. 243
    • Beatty, A.M.1
  • 11
    • 5644290035 scopus 로고
    • S. C. Zimmerman and B. F. Duerr, J. Org. Chem., 1992, 57, 2215; M. Gallant, M. T. P. Viet and J. D. Wuest, J. Org. Chem., 1991, 56, 2284; Y. Ducharme and J. D. Wuest, J. Org. Chem., 1988, 53, 5789.
    • (1992) J. Org. Chem. , vol.57 , pp. 2215
    • Zimmerman, S.C.1    Duerr, B.F.2
  • 12
    • 0007624696 scopus 로고
    • S. C. Zimmerman and B. F. Duerr, J. Org. Chem., 1992, 57, 2215; M. Gallant, M. T. P. Viet and J. D. Wuest, J. Org. Chem., 1991, 56, 2284; Y. Ducharme and J. D. Wuest, J. Org. Chem., 1988, 53, 5789.
    • (1991) J. Org. Chem. , vol.56 , pp. 2284
    • Gallant, M.1    Viet, M.T.P.2    Wuest, J.D.3
  • 13
    • 0000143458 scopus 로고
    • S. C. Zimmerman and B. F. Duerr, J. Org. Chem., 1992, 57, 2215; M. Gallant, M. T. P. Viet and J. D. Wuest, J. Org. Chem., 1991, 56, 2284; Y. Ducharme and J. D. Wuest, J. Org. Chem., 1988, 53, 5789.
    • (1988) J. Org. Chem. , vol.53 , pp. 5789
    • Ducharme, Y.1    Wuest, J.D.2
  • 14
    • 1242285039 scopus 로고    scopus 로고
    • T. Olszewska, M. Gdaniec and T. Polonski, J. Org. Chem., 2004, 69, 1248; Y. Du, C. J. Creighton, B. A. Tounge and A. B. Reitz, Org. Lett., 2004, 6, 309; M. R. Edwards, W. Jones and W. D. S. Motherwell, Cryst. Eng., 2002, 5, 25; C. B. Aakeröy, A. M. Beatty, M. Nieuwenhuyzen and M. Zou, Tetrahedron, 2000, 56, 6693; E. Murguly, R. McDonald and N. R. Branda, Org. Lett., 2000, 2, 3169; M. Akazome, S. Suzuki, Y. Shimizu, K. Henmi and K. Ogura, J. Org. Chem., 2000, 65, 6917; M. Simard, D. Su and J. D. Wuest, J. Am. Chem. Soc., 1991, 113, 4696.
    • (2004) J. Org. Chem. , vol.69 , pp. 1248
    • Olszewska, T.1    Gdaniec, M.2    Polonski, T.3
  • 15
    • 1342306686 scopus 로고    scopus 로고
    • T. Olszewska, M. Gdaniec and T. Polonski, J. Org. Chem., 2004, 69, 1248; Y. Du, C. J. Creighton, B. A. Tounge and A. B. Reitz, Org. Lett., 2004, 6, 309; M. R. Edwards, W. Jones and W. D. S. Motherwell, Cryst. Eng., 2002, 5, 25; C. B. Aakeröy, A. M. Beatty, M. Nieuwenhuyzen and M. Zou, Tetrahedron, 2000, 56, 6693; E. Murguly, R. McDonald and N. R. Branda, Org. Lett., 2000, 2, 3169; M. Akazome, S. Suzuki, Y. Shimizu, K. Henmi and K. Ogura, J. Org. Chem., 2000, 65, 6917; M. Simard, D. Su and J. D. Wuest, J. Am. Chem. Soc., 1991, 113, 4696.
    • (2004) Org. Lett. , vol.6 , pp. 309
    • Du, Y.1    Creighton, C.J.2    Tounge, B.A.3    Reitz, A.B.4
  • 16
    • 0036502190 scopus 로고    scopus 로고
    • T. Olszewska, M. Gdaniec and T. Polonski, J. Org. Chem., 2004, 69, 1248; Y. Du, C. J. Creighton, B. A. Tounge and A. B. Reitz, Org. Lett., 2004, 6, 309; M. R. Edwards, W. Jones and W. D. S. Motherwell, Cryst. Eng., 2002, 5, 25; C. B. Aakeröy, A. M. Beatty, M. Nieuwenhuyzen and M. Zou, Tetrahedron, 2000, 56, 6693; E. Murguly, R. McDonald and N. R. Branda, Org. Lett., 2000, 2, 3169; M. Akazome, S. Suzuki, Y. Shimizu, K. Henmi and K. Ogura, J. Org. Chem., 2000, 65, 6917; M. Simard, D. Su and J. D. Wuest, J. Am. Chem. Soc., 1991, 113, 4696.
    • (2002) Cryst. Eng. , vol.5 , pp. 25
    • Edwards, M.R.1    Jones, W.2    Motherwell, W.D.S.3
  • 17
    • 0033822472 scopus 로고    scopus 로고
    • T. Olszewska, M. Gdaniec and T. Polonski, J. Org. Chem., 2004, 69, 1248; Y. Du, C. J. Creighton, B. A. Tounge and A. B. Reitz, Org. Lett., 2004, 6, 309; M. R. Edwards, W. Jones and W. D. S. Motherwell, Cryst. Eng., 2002, 5, 25; C. B. Aakeröy, A. M. Beatty, M. Nieuwenhuyzen and M. Zou, Tetrahedron, 2000, 56, 6693; E. Murguly, R. McDonald and N. R. Branda, Org. Lett., 2000, 2, 3169; M. Akazome, S. Suzuki, Y. Shimizu, K. Henmi and K. Ogura, J. Org. Chem., 2000, 65, 6917; M. Simard, D. Su and J. D. Wuest, J. Am. Chem. Soc., 1991, 113, 4696.
    • (2000) Tetrahedron , vol.56 , pp. 6693
    • Aakeröy, C.B.1    Beatty, A.M.2    Nieuwenhuyzen, M.3    Zou, M.4
  • 18
    • 0000492788 scopus 로고    scopus 로고
    • T. Olszewska, M. Gdaniec and T. Polonski, J. Org. Chem., 2004, 69, 1248; Y. Du, C. J. Creighton, B. A. Tounge and A. B. Reitz, Org. Lett., 2004, 6, 309; M. R. Edwards, W. Jones and W. D. S. Motherwell, Cryst. Eng., 2002, 5, 25; C. B. Aakeröy, A. M. Beatty, M. Nieuwenhuyzen and M. Zou, Tetrahedron, 2000, 56, 6693; E. Murguly, R. McDonald and N. R. Branda, Org. Lett., 2000, 2, 3169; M. Akazome, S. Suzuki, Y. Shimizu, K. Henmi and K. Ogura, J. Org. Chem., 2000, 65, 6917; M. Simard, D. Su and J. D. Wuest, J. Am. Chem. Soc., 1991, 113, 4696.
    • (2000) Org. Lett. , vol.2 , pp. 3169
    • Murguly, E.1    McDonald, R.2    Branda, N.R.3
  • 19
    • 0034693120 scopus 로고    scopus 로고
    • T. Olszewska, M. Gdaniec and T. Polonski, J. Org. Chem., 2004, 69, 1248; Y. Du, C. J. Creighton, B. A. Tounge and A. B. Reitz, Org. Lett., 2004, 6, 309; M. R. Edwards, W. Jones and W. D. S. Motherwell, Cryst. Eng., 2002, 5, 25; C. B. Aakeröy, A. M. Beatty, M. Nieuwenhuyzen and M. Zou, Tetrahedron, 2000, 56, 6693; E. Murguly, R. McDonald and N. R. Branda, Org. Lett., 2000, 2, 3169; M. Akazome, S. Suzuki, Y. Shimizu, K. Henmi and K. Ogura, J. Org. Chem., 2000, 65, 6917; M. Simard, D. Su and J. D. Wuest, J. Am. Chem. Soc., 1991, 113, 4696.
    • (2000) J. Org. Chem. , vol.65 , pp. 6917
    • Akazome, M.1    Suzuki, S.2    Shimizu, Y.3    Henmi, K.4    Ogura, K.5
  • 20
    • 12044251859 scopus 로고
    • T. Olszewska, M. Gdaniec and T. Polonski, J. Org. Chem., 2004, 69, 1248; Y. Du, C. J. Creighton, B. A. Tounge and A. B. Reitz, Org. Lett., 2004, 6, 309; M. R. Edwards, W. Jones and W. D. S. Motherwell, Cryst. Eng., 2002, 5, 25; C. B. Aakeröy, A. M. Beatty, M. Nieuwenhuyzen and M. Zou, Tetrahedron, 2000, 56, 6693; E. Murguly, R. McDonald and N. R. Branda, Org. Lett., 2000, 2, 3169; M. Akazome, S. Suzuki, Y. Shimizu, K. Henmi and K. Ogura, J. Org. Chem., 2000, 65, 6917; M. Simard, D. Su and J. D. Wuest, J. Am. Chem. Soc., 1991, 113, 4696.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 4696
    • Simard, M.1    Su, D.2    Wuest, J.D.3
  • 22
    • 0000688914 scopus 로고
    • M. Munakata, L. P. Wu, M. Yamamoto, T. Kuroda-Sowa and M. Maekawa, J. Am. Chem. Soc., 1996, 118, 3117; S. R. Breeze and S. Wang, Inorg. Chem., 1993, 32, 5981.
    • (1993) Inorg. Chem. , vol.32 , pp. 5981
    • Breeze, S.R.1    Wang, S.2
  • 23
    • 0035006081 scopus 로고    scopus 로고
    • D. G. Kurth, K. M. Fromm and J.-M. Lehn, Eur. J. Inorg. Chem., 2001, 1523; E. Breuning, U. Ziener, J.-M. Lehn, E. Wegelius and K. Rissanen, Eur. J. Inorg. Chem., 2001, 1515; U. Ziener, E. Breuning, J.-M. Lehn, E. Wegelius, K. Rissanen, G. Baum, D. Fenske and G. Vaughan, Chem.-Eur. J., 2000, 6, 4132.
    • (2001) Eur. J. Inorg. Chem. , pp. 1523
    • Kurth, D.G.1    Fromm, K.M.2    Lehn, J.-M.3
  • 24
    • 0034995676 scopus 로고    scopus 로고
    • D. G. Kurth, K. M. Fromm and J.-M. Lehn, Eur. J. Inorg. Chem., 2001, 1523; E. Breuning, U. Ziener, J.-M. Lehn, E. Wegelius and K. Rissanen, Eur. J. Inorg. Chem., 2001, 1515; U. Ziener, E. Breuning, J.-M. Lehn, E. Wegelius, K. Rissanen, G. Baum, D. Fenske and G. Vaughan, Chem.-Eur. J., 2000, 6, 4132.
    • (2001) Eur. J. Inorg. Chem. , pp. 1515
    • Breuning, E.1    Ziener, U.2    Lehn, J.-M.3    Wegelius, E.4    Rissanen, K.5
  • 26
    • 16244396302 scopus 로고    scopus 로고
    • note
    • Janus was the Roman god of change and transition. He had two faces looking in opposite directions, hence the analogy with 1.
  • 31
    • 0000072771 scopus 로고    scopus 로고
    • For a discussion on Z′ and crystal packing frequencies see: T. Steiner, Acta Crystallogr., Sect. B, 2000, 56, 673; C. P. Brock, Chem. Mater., 1994, 6, 1118.
    • (2000) Acta Crystallogr., Sect. B , vol.56 , pp. 673
    • Steiner, T.1
  • 32
    • 26744461416 scopus 로고
    • For a discussion on Z′ and crystal packing frequencies see: T. Steiner, Acta Crystallogr., Sect. B, 2000, 56, 673; C. P. Brock, Chem. Mater., 1994, 6, 1118.
    • (1994) Chem. Mater. , vol.6 , pp. 1118
    • Brock, C.P.1
  • 33
  • 36
    • 0038621511 scopus 로고    scopus 로고
    • For selected hydrogen bonded structures see: D. Paul, F. Melin, C. Hirtz, J. Wytko, P. Ochsenbein, M. Bonin, K. Schenk, P. Maltese and J. Weiss, Inorg. Chem., 2003, 42, 3779; E. S. Lavender, R. M. Gregson, G. Ferguson and C. Glidewell, Acta Crystallogr., Sect. C, 1999, 55, 751; E. García- Martínez, E. M. Vázquez-López and D. G. Tuck, Acta Crystallogr., Sect. C, 1998, 54, 840; Y.-P. Tian, C.-Y. Duan, X.-X. Xu and X.-Z. You, Acta Crystallogr., Sect. C, 1995, 51, 2309; W. H. Watson, J. Galloy, F. Vögtle and W. M. Müller, Acta Crystallogr., Sect. C, 1984, 40, 200.
    • (2003) Inorg. Chem. , vol.42 , pp. 3779
    • Paul, D.1    Melin, F.2    Hirtz, C.3    Wytko, J.4    Ochsenbein, P.5    Bonin, M.6    Schenk, K.7    Maltese, P.8    Weiss, J.9
  • 37
    • 0002784684 scopus 로고    scopus 로고
    • For selected hydrogen bonded structures see: D. Paul, F. Melin, C. Hirtz, J. Wytko, P. Ochsenbein, M. Bonin, K. Schenk, P. Maltese and J. Weiss, Inorg. Chem., 2003, 42, 3779; E. S. Lavender, R. M. Gregson, G. Ferguson and C. Glidewell, Acta Crystallogr., Sect. C, 1999, 55, 751; E. García- Martínez, E. M. Vázquez-López and D. G. Tuck, Acta Crystallogr., Sect. C, 1998, 54, 840; Y.-P. Tian, C.-Y. Duan, X.-X. Xu and X.-Z. You, Acta Crystallogr., Sect. C, 1995, 51, 2309; W. H. Watson, J. Galloy, F. Vögtle and W. M. Müller, Acta Crystallogr., Sect. C, 1984, 40, 200.
    • (1999) Acta Crystallogr., Sect. C , vol.55 , pp. 751
    • Lavender, E.S.1    Gregson, R.M.2    Ferguson, G.3    Glidewell, C.4
  • 38
    • 11744304117 scopus 로고    scopus 로고
    • For selected hydrogen bonded structures see: D. Paul, F. Melin, C. Hirtz, J. Wytko, P. Ochsenbein, M. Bonin, K. Schenk, P. Maltese and J. Weiss, Inorg. Chem., 2003, 42, 3779; E. S. Lavender, R. M. Gregson, G. Ferguson and C. Glidewell, Acta Crystallogr., Sect. C, 1999, 55, 751; E. García- Martínez, E. M. Vázquez-López and D. G. Tuck, Acta Crystallogr., Sect. C, 1998, 54, 840; Y.-P. Tian, C.-Y. Duan, X.-X. Xu and X.-Z. You, Acta Crystallogr., Sect. C, 1995, 51, 2309; W. H. Watson, J. Galloy, F. Vögtle and W. M. Müller, Acta Crystallogr., Sect. C, 1984, 40, 200.
    • (1998) Acta Crystallogr., Sect. C , vol.54 , pp. 840
    • García-Martínez, E.1    Vázquez-López, E.M.2    Tuck, D.G.3
  • 39
    • 0004163683 scopus 로고
    • For selected hydrogen bonded structures see: D. Paul, F. Melin, C. Hirtz, J. Wytko, P. Ochsenbein, M. Bonin, K. Schenk, P. Maltese and J. Weiss, Inorg. Chem., 2003, 42, 3779; E. S. Lavender, R. M. Gregson, G. Ferguson and C. Glidewell, Acta Crystallogr., Sect. C, 1999, 55, 751; E. García- Martínez, E. M. Vázquez-López and D. G. Tuck, Acta Crystallogr., Sect. C, 1998, 54, 840; Y.-P. Tian, C.-Y. Duan, X.-X. Xu and X.-Z. You, Acta Crystallogr., Sect. C, 1995, 51, 2309; W. H. Watson, J. Galloy, F. Vögtle and W. M. Müller, Acta Crystallogr., Sect. C, 1984, 40, 200.
    • (1995) Acta Crystallogr., Sect. C , vol.51 , pp. 2309
    • Tian, Y.-P.1    Duan, C.-Y.2    Xu, X.-X.3    You, X.-Z.4
  • 40
    • 16244396929 scopus 로고
    • For selected hydrogen bonded structures see: D. Paul, F. Melin, C. Hirtz, J. Wytko, P. Ochsenbein, M. Bonin, K. Schenk, P. Maltese and J. Weiss, Inorg. Chem., 2003, 42, 3779; E. S. Lavender, R. M. Gregson, G. Ferguson and C. Glidewell, Acta Crystallogr., Sect. C, 1999, 55, 751; E. García- Martínez, E. M. Vázquez-López and D. G. Tuck, Acta Crystallogr., Sect. C, 1998, 54, 840; Y.-P. Tian, C.-Y. Duan, X.-X. Xu and X.-Z. You, Acta Crystallogr., Sect. C, 1995, 51, 2309; W. H. Watson, J. Galloy, F. Vögtle and W. M. Müller, Acta Crystallogr., Sect. C, 1984, 40, 200.
    • (1984) Acta Crystallogr., Sect. C , vol.40 , pp. 200
    • Watson, W.H.1    Galloy, J.2    Vögtle, F.3    Müller, W.M.4
  • 43
    • 0035263321 scopus 로고    scopus 로고
    • The literature does contain examples where the cis-amide motif fails to form the hydrogen bonded dimer in the solid state, see: E. F. Maverick, P. L. Wash and D. A. Lightner, Acta Crystallogr., Sect. C, 2001, 57, 284; É. Boucher, M. Simard and J. D. Wuest. J. Org. Chem., 1995, 60, 1408; M.-J. Brienne, J. Gabard, M. Leclercq, J.-M. Lehn, M. Cesario, C. Pascard, M. Chevé and G. Dutruc-Rosset, Tetrahedron Lett., 1994, 35, 8157.
    • (2001) Acta Crystallogr., Sect. C , vol.57 , pp. 284
    • Maverick, E.F.1    Wash, P.L.2    Lightner, D.A.3
  • 44
    • 0000620586 scopus 로고
    • The literature does contain examples where the cis-amide motif fails to form the hydrogen bonded dimer in the solid state, see: E. F. Maverick, P. L. Wash and D. A. Lightner, Acta Crystallogr., Sect. C, 2001, 57, 284; É. Boucher, M. Simard and J. D. Wuest. J. Org. Chem., 1995, 60, 1408; M.-J. Brienne, J. Gabard, M. Leclercq, J.-M. Lehn, M. Cesario, C. Pascard, M. Chevé and G. Dutruc-Rosset, Tetrahedron Lett., 1994, 35, 8157.
    • (1995) J. Org. Chem. , vol.60 , pp. 1408
    • Boucher, É.1    Simard, M.2    Wuest, J.D.3
  • 45
    • 0027945669 scopus 로고
    • The literature does contain examples where the cis-amide motif fails to form the hydrogen bonded dimer in the solid state, see: E. F. Maverick, P. L. Wash and D. A. Lightner, Acta Crystallogr., Sect. C, 2001, 57, 284; É. Boucher, M. Simard and J. D. Wuest. J. Org. Chem., 1995, 60, 1408; M.-J. Brienne, J. Gabard, M. Leclercq, J.-M. Lehn, M. Cesario, C. Pascard, M. Chevé and G. Dutruc-Rosset, Tetrahedron Lett., 1994, 35, 8157.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 8157
    • Brienne, M.-J.1    Gabard, J.2    Leclercq, M.3    Lehn, J.-M.4    Cesario, M.5    Pascard, C.6    Chevé, M.7    Dutruc-Rosset, G.8


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