Synthesis of new thiopyrylocyanines incorporated thiopyrano[2,3-b]indole ring as the main constituent

Heterocycles

Volumn 57, Issue 12, 2002, Pages 2227-2230

  Tominaga, Yoshinori ^a   Shigemitsu, Yasuhiro ^b   Hirayama, Shun ichi ^c  

^a NAGASAKI UNIVERSITY   (Japan)

^b Technology Center of Nagasaki   (Japan)

^c SASEBO NATIONAL COLLEGE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CYANINE DYE; DICARBOXYLIC ACID DERIVATIVE; DIMETHYLACETYLENEDICARBOXYLATE; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; METHYL 1,2 DIMETHYLINDOLE 3 DITHIOCARBOXYLATE; THIOPYRANO[2,3 B]INDOLE; THIOPYRYLOCYANINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; PRODUCTIVITY; REACTION ANALYSIS; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0036899692     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-02-9612     Document Type: Article

References (20)

1. a) A. T. Petera and H. S. Freeman, "Colour Chemistry: The Design and Synthesis of Organic Dyes and Pigments," Advances in Colour Chemistry Series, Elsevier Applied Science, New York, 1991;
2. b) D. R. Waring and G. Halls, "The Chemistry and Application of Dyes," Plenum Press, New York, 1991;
3. c) J. Fabian, H. Nakazumi, and M. Matsuoka, Chem. Rev., 1992, 92, 1197;
4. d) S. G. R. Guinot, J. D. Hepworth, and M. Wainwright, J. Chem. Soc., Perkin Trans. 2, 1998, 2972;
5. d) Y. Matsuda, K. Katou, H. Matsumoto, S. Ide, K. Takahashi, K. Torisu, K. Furuno, and S. Maeda, Yakugaku Zasshi, 1992, 112, 42 and references cited therein.
6. C. Kanony, B. Akerman, and E. M. Tuite, J. Am. Chem. Soc., 2001, 123, 7985.
7. a) M. Mizoguchi, M. Ishiyama, M. Shiga, and K. Sasamoto, Bunseki Kagaku, 1996, 45, 111;
8. b) M. Mizoguchi, M. Shiga, and K. Sasamoto, Chem. Pharm. Bull., 1993, 41, 620;
9. c) K. L. Cheng, K. Ueno, and T. Imamura, "Handbook of Organic Analytical Reagents," CRC Press, Inc., Boca Raton, p. 267, 1982.
10. a) Y. Tominaga, K. Komiya, S. Itonaga, N. Yoshioka, S. Kataoka, K. Sasaki, and T. Hirota, Heterocycles, 1997, 46, 41;
11. b) Y. Tominaga, S. Itonaga, T. Kouno, and Y. Shigemitsu, Heterocycles, 2001, 55, 1447.
12. Y. Tominaga, R. Natsuki, Y. Matsuda, and G. Kobayashi, Chem. Pharm. Bull., 1973, 21, 2770.
13. Though the stereochemistry of the products has not been decided, the structures shown in the figure have been estimated from the NMR spectra and the result of calculation by MOPAC.
14. +).
15. 3COOD) δ: 3.17 (3H, s, Me), 4.13 (3H, s, NMe), 4.14 (3H, s, OMe), (3H, s, OMe), 7.77 (1H, t, J=8.2 Hz, 7-H), 7.89 (1H, d, J=8.2 Hz, 8-H), 7.96 (1H, t, J=8.2 Hz, 9-H), 8.45 (1H, d, J=8.2 Hz, 6-H).
16. +, 100).
17. ++1).
18. 3) δ: 3.88 (3H, s, NMe), 3.97 (3H, s, OMe), 4.04 (3H, s, OMe), 6.30 (1H, d, J=12.4 Hz, C=H), 7.22-7.44 (3H, m, 7, 8, 9-H), 7.74(1H, d, J=8.2 Hz, 6-H), 8.24 (1H, d, J=12.4 Hz, C=H).
19. +).
20. +).