Synthesis of substituted phenothiazines analogous to methylene blue by electrophilic and nucleophilic aromatic substitutions in tandem. A mechanistic perspective

Tetrahedron

Volumn 53, Issue 29, 1997, Pages 10083-10092

  Leventis, Nicholas ^a   Chen, Muguo ^a   Sotiriou Leventis, Chariklia ^a  

^a MISSOURI UNIVERSITY OF SCIENCE AND TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHENOTHIAZINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; SPECTROPHOTOMETRY;

EID: 0030803834     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00349-9     Document Type: Article

References (34)

1. (a) Frierz-David, H. E.; Blangey, L. Fundamental Processes of Dye Chemistry, Interscience Publishers, Inc.: New York, 1949; p. 311;
2. (b) Zollinger H. Color Chemistry, Synthesis, Properties and Applications of Organic Dyes and Pigments, VCH Publishers: New York, 1987; p. 70;
3. (c) The Chemistry and Application of Dyes, Waring, D. R.; Hallas, G. Eds.; Plenum Press: New York, 1990.
4. Indicators, Bishop, E. Ed.; Pergamon Press: New York, 1972; p. 503.
5. Caro, German Patent No. 1,886 (1877).
6. (a) Tuite, E.; Norden, B. J. Am. Chem. Soc., 1994, 116, 7548;
7. (b) Hoppe, R.; Schulz-Ekloff, G.; Wohrle, D.; Kirschhock, C.; Fuess, H.; Uytterhoeven, L.; Schoonheydt, R. Advanced Materials, 1995, 7, 61;
8. (c) Ye, J.; Baldwin, R. P. Anal. Chem., 1988, 60, 2263;
9. (d) Kuwabata, S.; Mitsui, K.; Yoneyama, H. J. Electrochem. Soc., 1992, 139, 1824.
10. Leventis, N.; Chen, M. Polym. Mater. Sci. Eng. Prepr., 1995, 73, 406.
11. Arkles, B. CHEMTECH, 1977, 7, 766.
12. Speier, J. L. Advan. Organometal. Chem., 1979, 17, 407.
13. March, J. Advanced Organic Chemistry Reactions Mechanisms and Structure, Fourth Edition, John Wiley & Sons: New York, 1992; p. 1188.
14. (a) Kehrmann, F. Ber., 1916, 49, 53;
15. (b) Kehrmann, F.; Diserens, L. Ber., 1915, 48, 318.
16. (a) The Chemistry of Synthetic Dyes and Pigments, Lubs, H. A. Ed.; ACS Monograph Series No. 127, Reinhold Publishing Co.: New York, 1955; p. 267;
17. (b) Bodea, C.; Silberg, I. In Advances in Heterocyclic Chemistry, Katritzky, A. R.; Boulton A. J. Eds.; Academic Press: New York, 1968; Vol. 9, p. 321;
18. (c) Fortin, R.; Guindon, Y.; Lau, C. K.; Rokach, J.; Yoakim, C. European Patent Application No. 0138481, Bulletin 85/17, 1985.
19. Found: C: 39.10; H, 1.90; N, 3.97; S, 8.76; Br, 46.52. Calculated for 7: C, 40.37; H, 1.98; N, 3.92; S, 8.98; Br, 44.75. The calculated values for 8 are given in the experimental section.
20. Chiu, H.; Reeves, P. C.; Biehl, E. R. J. Heterocyclic Chem., 1976, 13, 77.
21. (a) Kim, K.; Shine, H. J. J. Org. Chem., 1974, 39, 2537;
22. (b) Shine, H. J.; Silber, J. J.; Bussey, R. J.; Okuyama, T. J. Org. Chem., 1972, 37, 2691;
23. (c) Murata, Y.; Shine, H. J. J. Org. Chem., 1969, 34, 3368;
24. (d) Silber, J. J.; Shine, H. J. J. Org. Chem., 1971, 36, 2923.
25. Bard, A. J.; Faulkner, L. R. Electrochemical Methods Fundamentals and Applications, John Wiley and Sons: New York, 1980; p. 699.
26. Cauquis, G.; Deronzier, A.; Lepage, J.-L.; Serve, D. Bull. Soc. Chim., 1977, 295.
27. Bodea, C.; Raileanu, M. Liebigs Ann. Chem., 1960, 631, 194.
28. Rabinowitch E.; Epstein, L. F. J. Am. Chem. Soc., 1941, 63, 69.
29. 19 we expect at least for Eq.[2] simple bimolecular kinetics where the slow step is the coordination of the amine to carbon. From this perspective, the first order kinetics of Fig.s 3A and 3B are interpreted as pseudounimolecular, and second order rate constants can be calculated.
30. Isaacs, N. Physical Organic Chemistry Second Edition, John Wiley and Sons: New York, 1995; p. 498.
31. Hammes, G. G. Principles of Chemical Kinetics, Academic Press Inc.: New York, 1978; p. 9.
32. In contact with air 8 turns to an insoluble purple-black material over a period of 2-3 days, while in DMF/0.1 M TBAP 8 shows an irreversible oxidation wave above 0.8 V vs. Ag/AgCl.
33. 15 low resolution FAB (3-NBA/Gly/TFA) m/z 286.0 (cation).
34. Cymerman-Craig, J.; Rogers, W. P.; Warwick, G. P. Austral. J. Chem., 1955, 8, 252.