Control of the fading properties of photochromic 3,3-diaryl-3H-naphtho[2,1-b]pyrans

Heterocycles

Volumn 60, Issue 4, 2003, Pages 843-855

  Gabbutt, Christopher D ^a   Heron, B Mark ^a   Instone, Alicia C ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

3H NAPHTHO[2,1 B]PYRAN DERIVATIVE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RING OPENING; SPECTROSCOPY; SYNTHESIS; ULTRAVIOLET RADIATION;

EID: 0037389826     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-02-9692     Document Type: Article

References (33)

1. D. A. Clarke, B. M. Heron, C. D. Gabbutt, J. D. Hepworth, S. M. Partington and S. N. Corns, PCT WO 98/45281, 1998 (Chem. Abstr., 1998, 129:317585); ibid, PCT WO 00/18755, 2000 (Chem. Abstr., 2000, 132:252460); V. D. Arsenov, A. M. Gorelik, V. A. Barachevsky and M. V. Alfimov, EP 1038870 A1, 2000 (Chem. Abstr., 2000, 133:268232); A. Kumar, US Patent 6353102 B1, 2002 (Chem. Abstr., 2002, 136:218337); T. Tanizawa, T. Hara, Y. Kawabata, J. Momoda and H. Nagoh, PCT WO 98/57943, 1998 (Chem. Abstr., 1999, 130:66392); M. Melzig and U. Weigand, PCT WO 99/24438, 1999 (Chem. Abstr., 1999, 130:353638); F. J. Hughes and E. A. Travnicek, US Patent 6337409B1, 2002 (Chem. Abstr., 2002, 136:8723).
2. D. A. Clarke, B. M. Heron, C. D. Gabbutt, J. D. Hepworth, S. M. Partington and S. N. Corns, PCT WO 98/45281, 1998 (Chem. Abstr., 1998, 129:317585); ibid, PCT WO 00/18755, 2000 (Chem. Abstr., 2000, 132:252460); V. D. Arsenov, A. M. Gorelik, V. A. Barachevsky and M. V. Alfimov, EP 1038870 A1, 2000 (Chem. Abstr., 2000, 133:268232); A. Kumar, US Patent 6353102 B1, 2002 (Chem. Abstr., 2002, 136:218337); T. Tanizawa, T. Hara, Y. Kawabata, J. Momoda and H. Nagoh, PCT WO 98/57943, 1998 (Chem. Abstr., 1999, 130:66392); M. Melzig and U. Weigand, PCT WO 99/24438, 1999 (Chem. Abstr., 1999, 130:353638); F. J. Hughes and E. A. Travnicek, US Patent 6337409B1, 2002 (Chem. Abstr., 2002, 136:8723).
3. D. A. Clarke, B. M. Heron, C. D. Gabbutt, J. D. Hepworth, S. M. Partington and S. N. Corns, PCT WO 98/45281, 1998 (Chem. Abstr., 1998, 129:317585); ibid, PCT WO 00/18755, 2000 (Chem. Abstr., 2000, 132:252460); V. D. Arsenov, A. M. Gorelik, V. A. Barachevsky and M. V. Alfimov, EP 1038870 A1, 2000 (Chem. Abstr., 2000, 133:268232); A. Kumar, US Patent 6353102 B1, 2002 (Chem. Abstr., 2002, 136:218337); T. Tanizawa, T. Hara, Y. Kawabata, J. Momoda and H. Nagoh, PCT WO 98/57943, 1998 (Chem. Abstr., 1999, 130:66392); M. Melzig and U. Weigand, PCT WO 99/24438, 1999 (Chem. Abstr., 1999, 130:353638); F. J. Hughes and E. A. Travnicek, US Patent 6337409B1, 2002 (Chem. Abstr., 2002, 136:8723).
4. D. A. Clarke, B. M. Heron, C. D. Gabbutt, J. D. Hepworth, S. M. Partington and S. N. Corns, PCT WO 98/45281, 1998 (Chem. Abstr., 1998, 129:317585); ibid, PCT WO 00/18755, 2000 (Chem. Abstr., 2000, 132:252460); V. D. Arsenov, A. M. Gorelik, V. A. Barachevsky and M. V. Alfimov, EP 1038870 A1, 2000 (Chem. Abstr., 2000, 133:268232); A. Kumar, US Patent 6353102 B1, 2002 (Chem. Abstr., 2002, 136:218337); T. Tanizawa, T. Hara, Y. Kawabata, J. Momoda and H. Nagoh, PCT WO 98/57943, 1998 (Chem. Abstr., 1999, 130:66392); M. Melzig and U. Weigand, PCT WO 99/24438, 1999 (Chem. Abstr., 1999, 130:353638); F. J. Hughes and E. A. Travnicek, US Patent 6337409B1, 2002 (Chem. Abstr., 2002, 136:8723).
5. D. A. Clarke, B. M. Heron, C. D. Gabbutt, J. D. Hepworth, S. M. Partington and S. N. Corns, PCT WO 98/45281, 1998 (Chem. Abstr., 1998, 129:317585); ibid, PCT WO 00/18755, 2000 (Chem. Abstr., 2000, 132:252460); V. D. Arsenov, A. M. Gorelik, V. A. Barachevsky and M. V. Alfimov, EP 1038870 A1, 2000 (Chem. Abstr., 2000, 133:268232); A. Kumar, US Patent 6353102 B1, 2002 (Chem. Abstr., 2002, 136:218337); T. Tanizawa, T. Hara, Y. Kawabata, J. Momoda and H. Nagoh, PCT WO 98/57943, 1998 (Chem. Abstr., 1999, 130:66392); M. Melzig and U. Weigand, PCT WO 99/24438, 1999 (Chem. Abstr., 1999, 130:353638); F. J. Hughes and E. A. Travnicek, US Patent 6337409B1, 2002 (Chem. Abstr., 2002, 136:8723).
6. D. A. Clarke, B. M. Heron, C. D. Gabbutt, J. D. Hepworth, S. M. Partington and S. N. Corns, PCT WO 98/45281, 1998 (Chem. Abstr., 1998, 129:317585); ibid, PCT WO 00/18755, 2000 (Chem. Abstr., 2000, 132:252460); V. D. Arsenov, A. M. Gorelik, V. A. Barachevsky and M. V. Alfimov, EP 1038870 A1, 2000 (Chem. Abstr., 2000, 133:268232); A. Kumar, US Patent 6353102 B1, 2002 (Chem. Abstr., 2002, 136:218337); T. Tanizawa, T. Hara, Y. Kawabata, J. Momoda and H. Nagoh, PCT WO 98/57943, 1998 (Chem. Abstr., 1999, 130:66392); M. Melzig and U. Weigand, PCT WO 99/24438, 1999 (Chem. Abstr., 1999, 130:353638); F. J. Hughes and E. A. Travnicek, US Patent 6337409B1, 2002 (Chem. Abstr., 2002, 136:8723).
7. D. A. Clarke, B. M. Heron, C. D. Gabbutt, J. D. Hepworth, S. M. Partington and S. N. Corns, PCT WO 98/45281, 1998 (Chem. Abstr., 1998, 129:317585); ibid, PCT WO 00/18755, 2000 (Chem. Abstr., 2000, 132:252460); V. D. Arsenov, A. M. Gorelik, V. A. Barachevsky and M. V. Alfimov, EP 1038870 A1, 2000 (Chem. Abstr., 2000, 133:268232); A. Kumar, US Patent 6353102 B1, 2002 (Chem. Abstr., 2002, 136:218337); T. Tanizawa, T. Hara, Y. Kawabata, J. Momoda and H. Nagoh, PCT WO 98/57943, 1998 (Chem. Abstr., 1999, 130:66392); M. Melzig and U. Weigand, PCT WO 99/24438, 1999 (Chem. Abstr., 1999, 130:353638); F. J. Hughes and E. A. Travnicek, US Patent 6337409B1, 2002 (Chem. Abstr., 2002, 136:8723).
8. Photochromism, Techniques of Chemistry, Volume 3, ed. by G. H. Brown, 1971, J. Wiley and Sons, New York; Photochromism: Molecules and Systems, Studies in Organic Chemistry, Volume 40, ed. By H. Dürr and H. BouasLaurent, Elsevier, Amsterdam, 1990; Organic Photochromic and Thermochromic Compounds, Volume 1 Main Photochromic Families, ed. by J. C. Crano and R. J. Guglielmetti, Plenum Press, New York, 1999; Organic Photochromic and Thermochromic Compounds, Volume 2 Physicochemical Studies, Biological Applications and Thermochromism, ed. by J. C. Crano and R. J. Guglielmetti, Plenum Press, New York, 1999; M. Irie (guest editor), Chem. Rev., 2000, 100, 1685.
9. Photochromism, Techniques of Chemistry, Volume 3, ed. by G. H. Brown, 1971, J. Wiley and Sons, New York; Photochromism: Molecules and Systems, Studies in Organic Chemistry, Volume 40, ed. By H. Dürr and H. BouasLaurent, Elsevier, Amsterdam, 1990; Organic Photochromic and Thermochromic Compounds, Volume 1 Main Photochromic Families, ed. by J. C. Crano and R. J. Guglielmetti, Plenum Press, New York, 1999; Organic Photochromic and Thermochromic Compounds, Volume 2 Physicochemical Studies, Biological Applications and Thermochromism, ed. by J. C. Crano and R. J. Guglielmetti, Plenum Press, New York, 1999; M. Irie (guest editor), Chem. Rev., 2000, 100, 1685.
10. Photochromism, Techniques of Chemistry, Volume 3, ed. by G. H. Brown, 1971, J. Wiley and Sons, New York; Photochromism: Molecules and Systems, Studies in Organic Chemistry, Volume 40, ed. By H. Dürr and H. BouasLaurent, Elsevier, Amsterdam, 1990; Organic Photochromic and Thermochromic Compounds, Volume 1 Main Photochromic Families, ed. by J. C. Crano and R. J. Guglielmetti, Plenum Press, New York, 1999; Organic Photochromic and Thermochromic Compounds, Volume 2 Physicochemical Studies, Biological Applications and Thermochromism, ed. by J. C. Crano and R. J. Guglielmetti, Plenum Press, New York, 1999; M. Irie (guest editor), Chem. Rev., 2000, 100, 1685.
11. Photochromism, Techniques of Chemistry, Volume 3, ed. by G. H. Brown, 1971, J. Wiley and Sons, New York; Photochromism: Molecules and Systems, Studies in Organic Chemistry, Volume 40, ed. By H. Dürr and H. BouasLaurent, Elsevier, Amsterdam, 1990; Organic Photochromic and Thermochromic Compounds, Volume 1 Main Photochromic Families, ed. by J. C. Crano and R. J. Guglielmetti, Plenum Press, New York, 1999; Organic Photochromic and Thermochromic Compounds, Volume 2 Physicochemical Studies, Biological Applications and Thermochromism, ed. by J. C. Crano and R. J. Guglielmetti, Plenum Press, New York, 1999; M. Irie (guest editor), Chem. Rev., 2000, 100, 1685.
12. Photochromism, Techniques of Chemistry, Volume 3, ed. by G. H. Brown, 1971, J. Wiley and Sons, New York; Photochromism: Molecules and Systems, Studies in Organic Chemistry, Volume 40, ed. By H. Dürr and H. BouasLaurent, Elsevier, Amsterdam, 1990; Organic Photochromic and Thermochromic Compounds, Volume 1 Main Photochromic Families, ed. by J. C. Crano and R. J. Guglielmetti, Plenum Press, New York, 1999; Organic Photochromic and Thermochromic Compounds, Volume 2 Physicochemical Studies, Biological Applications and Thermochromism, ed. by J. C. Crano and R. J. Guglielmetti, Plenum Press, New York, 1999; M. Irie (guest editor), Chem. Rev., 2000, 100, 1685.
13. J. D. Hepworth, C. D. Gabbutt and B. M. Heron, Colour Science '98, ed. by J. Griffiths, University of Leeds, 1999, p.161; B. Van Gemert in Organic Photochromic and Thermochromic Compounds, Volume 1 Main Photochromic Families, ed. by J. C. Crano and R. J. Guglielmetti, Plenum Press, New York, 1999, p. 111.
14. J. D. Hepworth, C. D. Gabbutt and B. M. Heron, Colour Science '98, ed. by J. Griffiths, University of Leeds, 1999, p.161; B. Van Gemert in Organic Photochromic and Thermochromic Compounds, Volume 1 Main Photochromic Families, ed. by J. C. Crano and R. J. Guglielmetti, Plenum Press, New York, 1999, p. 111.
15. M. Rickwood, K. E. Smith, C. D. Gabbutt and J. D. Hepworth, PCT WO 94/22850, 1994 (Chem. Abstr., 1995, 122:31328); D. A. Clarke, B. M. Heron, C. D. Gabbutt, J. D. Hepworth, S. M. Partington and S. N. Corns, PCT WO 98/45281, 1998 (Chem. Abstr., 1998, 129:317585).
16. M. Rickwood, K. E. Smith, C. D. Gabbutt and J. D. Hepworth, PCT WO 94/22850, 1994 (Chem. Abstr., 1995, 122:31328); D. A. Clarke, B. M. Heron, C. D. Gabbutt, J. D. Hepworth, S. M. Partington and S. N. Corns, PCT WO 98/45281, 1998 (Chem. Abstr., 1998, 129:317585).
17. B. Van Gemert and M. P. Bergomi, US Patent No. 5066818, 1991 (Chem. Abstr., 1992, 116:194155).
18. For examples of the synthesis of benzophenones utilising a Vilsmeier reaction see: R. W. R. Humphreys and D. R. Arnold, Can. J. Chem., 1979, 57, 2652; J. R. DoAmaral, E. J. Blanz Jr. and F. A. French, J. Med. Chem., 1969, 12, 21; W. B. Tuemmler and B. S. Wildi, J. Am. Chem. Soc., 1958, 80, 3772.
19. For examples of the synthesis of benzophenones utilising a Vilsmeier reaction see: R. W. R. Humphreys and D. R. Arnold, Can. J. Chem., 1979, 57, 2652; J. R. DoAmaral, E. J. Blanz Jr. and F. A. French, J. Med. Chem., 1969, 12, 21; W. B. Tuemmler and B. S. Wildi, J. Am. Chem. Soc., 1958, 80, 3772.
20. For examples of the synthesis of benzophenones utilising a Vilsmeier reaction see: R. W. R. Humphreys and D. R. Arnold, Can. J. Chem., 1979, 57, 2652; J. R. DoAmaral, E. J. Blanz Jr. and F. A. French, J. Med. Chem., 1969, 12, 21; W. B. Tuemmler and B. S. Wildi, J. Am. Chem. Soc., 1958, 80, 3772.
21. G. Höfle, W. Steglich and H. Vorbrüggen, Angew. Chem., Int. Ed. Engl., 1978, 17, 569; E. F. V. Scriven, Chem. Soc. Rev., 1983, 12, 129.
22. G. Höfle, W. Steglich and H. Vorbrüggen, Angew. Chem., Int. Ed. Engl., 1978, 17, 569; E. F. V. Scriven, Chem. Soc. Rev., 1983, 12, 129.
23. C. D. Gabbutt, J. D. Hepworth, B. M. Heron, S. M. Partington and D. A. Thomas, Dyes and Pigments, 2001, 49, 65.
24. J. D. Hepworth, C. D. Gabbutt and B. M. Heron in Comprehensive Heterocyclic Chemistry II, ed. by A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon, Oxford, 1996, Volume 5, p.310.
25. J. D. Hepworth, C. D. Gabbutt and B. M. Heron, Dyes and Pigments, 2002, 54, 79.
26. W. Zhao and E. M. Carreira, J. Am. Chem. Soc., 2002, 124, 1582.
27. S. Delbaere, Y. Teral, C. Bochu, M. Campredon and G. Vermeersch, Mag. Reson. Chem., 1999, 37, 159.
28. G. Hallas, J. Soc. Dyers and Colour., 1967, 83, 368.
29. W. C. Still, M. Khan and A. Mitra, J. Org. Chem., 1978, 43, 2923.
30. J. F. Bunnett and S. Y. Yih, J. Am. Chem. Soc., 1961, 83, 3807.
31. N. G. Kundu and M. W. Khan, Tetrahedron, 2000, 56, 4777.
32. D. M. Phatak and G. V. Jadhav, J. Ind. Chem. Soc., 1958, 35, 717.
33. P. Grammaticakis, Bull. Soc. Chim. Fr., 1963, 862.