One-pot synthesis of 1,4-dichlorophenazines

Tetrahedron

Volumn 53, Issue 17, 1997, Pages 6183-6194

  Guirado, Antonio ^a   Cerezo, Alfredo ^a   Ramírez De Arellano, M Carmen ^a  

^a UNIVERSITY OF MURCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOCHLORINE DERIVATIVE; PHENAZINE DERIVATIVE;

ARTICLE; CHLORINATION; CRYSTALLOGRAPHY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030897454     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00275-5     Document Type: Article

References (33)

1. The chemistry of phenazines has been excellently reviewed: (a) Swan, G.A.; Felton, D.G.I. Phenazines, Chemistry of Heterocyclic Compounds; Wiley: 1957; Vol. 11; (b) Porter, A.E.A. in Comprehensive Heterocyclic Chemistry; Katritzky, A.; Rees, C.; Potts, K. Eds.; Pergamon Press: 1984; Vol. 3; p. 157; (c) McCullough, K.J. in Rodd's Chemistry of Carbon Compounds; Ansell, M.F. Ed.; Elsevier: 1989; Vol 4; Part I J; p. 354.
2. The chemistry of phenazines has been excellently reviewed: (a) Swan, G.A.; Felton, D.G.I. Phenazines, Chemistry of Heterocyclic Compounds; Wiley: 1957; Vol. 11; (b) Porter, A.E.A. in Comprehensive Heterocyclic Chemistry; Katritzky, A.; Rees, C.; Potts, K. Eds.; Pergamon Press: 1984; Vol. 3; p. 157; (c) McCullough, K.J. in Rodd's Chemistry of Carbon Compounds; Ansell, M.F. Ed.; Elsevier: 1989; Vol 4; Part I J; p. 354.
3. The chemistry of phenazines has been excellently reviewed: (a) Swan, G.A.; Felton, D.G.I. Phenazines, Chemistry of Heterocyclic Compounds; Wiley: 1957; Vol. 11; (b) Porter, A.E.A. in Comprehensive Heterocyclic Chemistry; Katritzky, A.; Rees, C.; Potts, K. Eds.; Pergamon Press: 1984; Vol. 3; p. 157; (c) McCullough, K.J. in Rodd's Chemistry of Carbon Compounds; Ansell, M.F. Ed.; Elsevier: 1989; Vol 4; Part I J; p. 354.
4. For example, Tada, M. Bull. Chem. Soc. Jpn. 1974, 47, 1803; Vivian, D. L. J. Org. Chem. 1956, 21, 565; Vivian, D. L. J. Amer. Chem. Soc. 1951, 73, 457; Vivian, D.L.; Hogart, R.M.; Belkin, M. J. Org. Chem., 1961, 26, 112; Tada, M. Bull. Chem. Soc. Jpn. 1978, 51, 3093; Pachter, J.; Kloetzel, M.C. J. Amer. Chem. Soc. 1952, 74, 971; Tada, M. Bull. Chem. Soc. Jpn. 1975, 48, 363 and references cited therein.
5. For example, Tada, M. Bull. Chem. Soc. Jpn. 1974, 47, 1803; Vivian, D. L. J. Org. Chem. 1956, 21, 565; Vivian, D. L. J. Amer. Chem. Soc. 1951, 73, 457; Vivian, D.L.; Hogart, R.M.; Belkin, M. J. Org. Chem., 1961, 26, 112; Tada, M. Bull. Chem. Soc. Jpn. 1978, 51, 3093; Pachter, J.; Kloetzel, M.C. J. Amer. Chem. Soc. 1952, 74, 971; Tada, M. Bull. Chem. Soc. Jpn. 1975, 48, 363 and references cited therein.
6. For example, Tada, M. Bull. Chem. Soc. Jpn. 1974, 47, 1803; Vivian, D. L. J. Org. Chem. 1956, 21, 565; Vivian, D. L. J. Amer. Chem. Soc. 1951, 73, 457; Vivian, D.L.; Hogart, R.M.; Belkin, M. J. Org. Chem., 1961, 26, 112; Tada, M. Bull. Chem. Soc. Jpn. 1978, 51, 3093; Pachter, J.; Kloetzel, M.C. J. Amer. Chem. Soc. 1952, 74, 971; Tada, M. Bull. Chem. Soc. Jpn. 1975, 48, 363 and references cited therein.
7. For example, Tada, M. Bull. Chem. Soc. Jpn. 1974, 47, 1803; Vivian, D. L. J. Org. Chem. 1956, 21, 565; Vivian, D. L. J. Amer. Chem. Soc. 1951, 73, 457; Vivian, D.L.; Hogart, R.M.; Belkin, M. J. Org. Chem., 1961, 26, 112; Tada, M. Bull. Chem. Soc. Jpn. 1978, 51, 3093; Pachter, J.; Kloetzel, M.C. J. Amer. Chem. Soc. 1952, 74, 971; Tada, M. Bull. Chem. Soc. Jpn. 1975, 48, 363 and references cited therein.
8. For example, Tada, M. Bull. Chem. Soc. Jpn. 1974, 47, 1803; Vivian, D. L. J. Org. Chem. 1956, 21, 565; Vivian, D. L. J. Amer. Chem. Soc. 1951, 73, 457; Vivian, D.L.; Hogart, R.M.; Belkin, M. J. Org. Chem., 1961, 26, 112; Tada, M. Bull. Chem. Soc. Jpn. 1978, 51, 3093; Pachter, J.; Kloetzel, M.C. J. Amer. Chem. Soc. 1952, 74, 971; Tada, M. Bull. Chem. Soc. Jpn. 1975, 48, 363 and references cited therein.
9. For example, Tada, M. Bull. Chem. Soc. Jpn. 1974, 47, 1803; Vivian, D. L. J. Org. Chem. 1956, 21, 565; Vivian, D. L. J. Amer. Chem. Soc. 1951, 73, 457; Vivian, D.L.; Hogart, R.M.; Belkin, M. J. Org. Chem., 1961, 26, 112; Tada, M. Bull. Chem. Soc. Jpn. 1978, 51, 3093; Pachter, J.; Kloetzel, M.C. J. Amer. Chem. Soc. 1952, 74, 971; Tada, M. Bull. Chem. Soc. Jpn. 1975, 48, 363 and references cited therein.
10. For example, Tada, M. Bull. Chem. Soc. Jpn. 1974, 47, 1803; Vivian, D. L. J. Org. Chem. 1956, 21, 565; Vivian, D. L. J. Amer. Chem. Soc. 1951, 73, 457; Vivian, D.L.; Hogart, R.M.; Belkin, M. J. Org. Chem., 1961, 26, 112; Tada, M. Bull. Chem. Soc. Jpn. 1978, 51, 3093; Pachter, J.; Kloetzel, M.C. J. Amer. Chem. Soc. 1952, 74, 971; Tada, M. Bull. Chem. Soc. Jpn. 1975, 48, 363 and references cited therein.
11. Cross, B.; Dunn, C.L.; Pyne, D.H.; Tipton, J.D. J. Sci. Fd Agric. 1969, 20, 8.
12. Ref. 1c, p. 355.
13. For example, Kitahara, T.; Kinoshita, Y.; Aono, S.; Miyake, M.; Watanabe, H.; Mori, K. Pure Appl. Chem. 1994, 66, 2083; Van't Land, C.W.; Mocek, U.; Floss, H.G. J. Org. Chem. 1993, 58, 6576; Geiger, A.; Keller-Schierlein, W.; Brandi, M.; Zähner, H. J. Antibiotics 1988, 41, 1542; Takahashi, K.; Takahashi, I.; Morimoto, M; Tomita, F. J. Antibiotics 1986, 39, 624; Ömura, S.; Eda, S.; Funayama, S.; Komiyama, K.; Takahashi, Y; Woodruff, H. B. J. Antibiotics 1989, 42, 1037; Lehn, J.-M.; Schmidt, F.; Vigneron, J.-P. Tetrahedron Lett. 1988, 29, 5255; Lehn, J.-M.; Schmidt, F.; Vigneron, J.-P. J. Heterocyclic Chem. 1990, 27, 1633.
14. For example, Kitahara, T.; Kinoshita, Y.; Aono, S.; Miyake, M.; Watanabe, H.; Mori, K. Pure Appl. Chem. 1994, 66, 2083; Van't Land, C.W.; Mocek, U.; Floss, H.G. J. Org. Chem. 1993, 58, 6576; Geiger, A.; Keller-Schierlein, W.; Brandi, M.; Zähner, H. J. Antibiotics 1988, 41, 1542; Takahashi, K.; Takahashi, I.; Morimoto, M; Tomita, F. J. Antibiotics 1986, 39, 624; Ömura, S.; Eda, S.; Funayama, S.; Komiyama, K.; Takahashi, Y; Woodruff, H. B. J. Antibiotics 1989, 42, 1037; Lehn, J.-M.; Schmidt, F.; Vigneron, J.-P. Tetrahedron Lett. 1988, 29, 5255; Lehn, J.-M.; Schmidt, F.; Vigneron, J.-P. J. Heterocyclic Chem. 1990, 27, 1633.
15. For example, Kitahara, T.; Kinoshita, Y.; Aono, S.; Miyake, M.; Watanabe, H.; Mori, K. Pure Appl. Chem. 1994, 66, 2083; Van't Land, C.W.; Mocek, U.; Floss, H.G. J. Org. Chem. 1993, 58, 6576; Geiger, A.; Keller-Schierlein, W.; Brandi, M.; Zähner, H. J. Antibiotics 1988, 41, 1542; Takahashi, K.; Takahashi, I.; Morimoto, M; Tomita, F. J. Antibiotics 1986, 39, 624; Ömura, S.; Eda, S.; Funayama, S.; Komiyama, K.; Takahashi, Y; Woodruff, H. B. J. Antibiotics 1989, 42, 1037; Lehn, J.-M.; Schmidt, F.; Vigneron, J.-P. Tetrahedron Lett. 1988, 29, 5255; Lehn, J.-M.; Schmidt, F.; Vigneron, J.-P. J. Heterocyclic Chem. 1990, 27, 1633.
16. For example, Kitahara, T.; Kinoshita, Y.; Aono, S.; Miyake, M.; Watanabe, H.; Mori, K. Pure Appl. Chem. 1994, 66, 2083; Van't Land, C.W.; Mocek, U.; Floss, H.G. J. Org. Chem. 1993, 58, 6576; Geiger, A.; Keller-Schierlein, W.; Brandi, M.; Zähner, H. J. Antibiotics 1988, 41, 1542; Takahashi, K.; Takahashi, I.; Morimoto, M; Tomita, F. J. Antibiotics 1986, 39, 624; Ömura, S.; Eda, S.; Funayama, S.; Komiyama, K.; Takahashi, Y; Woodruff, H. B. J. Antibiotics 1989, 42, 1037; Lehn, J.-M.; Schmidt, F.; Vigneron, J.-P. Tetrahedron Lett. 1988, 29, 5255; Lehn, J.-M.; Schmidt, F.; Vigneron, J.-P. J. Heterocyclic Chem. 1990, 27, 1633.
17. For example, Kitahara, T.; Kinoshita, Y.; Aono, S.; Miyake, M.; Watanabe, H.; Mori, K. Pure Appl. Chem. 1994, 66, 2083; Van't Land, C.W.; Mocek, U.; Floss, H.G. J. Org. Chem. 1993, 58, 6576; Geiger, A.; Keller-Schierlein, W.; Brandi, M.; Zähner, H. J. Antibiotics 1988, 41, 1542; Takahashi, K.; Takahashi, I.; Morimoto, M; Tomita, F. J. Antibiotics 1986, 39, 624; Ömura, S.; Eda, S.; Funayama, S.; Komiyama, K.; Takahashi, Y; Woodruff, H. B. J. Antibiotics 1989, 42, 1037; Lehn, J.-M.; Schmidt, F.; Vigneron, J.-P. Tetrahedron Lett. 1988, 29, 5255; Lehn, J.-M.; Schmidt, F.; Vigneron, J.-P. J. Heterocyclic Chem. 1990, 27, 1633.
18. For example, Kitahara, T.; Kinoshita, Y.; Aono, S.; Miyake, M.; Watanabe, H.; Mori, K. Pure Appl. Chem. 1994, 66, 2083; Van't Land, C.W.; Mocek, U.; Floss, H.G. J. Org. Chem. 1993, 58, 6576; Geiger, A.; Keller-Schierlein, W.; Brandi, M.; Zähner, H. J. Antibiotics 1988, 41, 1542; Takahashi, K.; Takahashi, I.; Morimoto, M; Tomita, F. J. Antibiotics 1986, 39, 624; Ömura, S.; Eda, S.; Funayama, S.; Komiyama, K.; Takahashi, Y; Woodruff, H. B. J. Antibiotics 1989, 42, 1037; Lehn, J.-M.; Schmidt, F.; Vigneron, J.-P. Tetrahedron Lett. 1988, 29, 5255; Lehn, J.-M.; Schmidt, F.; Vigneron, J.-P. J. Heterocyclic Chem. 1990, 27, 1633.
19. For example, Kitahara, T.; Kinoshita, Y.; Aono, S.; Miyake, M.; Watanabe, H.; Mori, K. Pure Appl. Chem. 1994, 66, 2083; Van't Land, C.W.; Mocek, U.; Floss, H.G. J. Org. Chem. 1993, 58, 6576; Geiger, A.; Keller-Schierlein, W.; Brandi, M.; Zähner, H. J. Antibiotics 1988, 41, 1542; Takahashi, K.; Takahashi, I.; Morimoto, M; Tomita, F. J. Antibiotics 1986, 39, 624; Ömura, S.; Eda, S.; Funayama, S.; Komiyama, K.; Takahashi, Y; Woodruff, H. B. J. Antibiotics 1989, 42, 1037; Lehn, J.-M.; Schmidt, F.; Vigneron, J.-P. Tetrahedron Lett. 1988, 29, 5255; Lehn, J.-M.; Schmidt, F.; Vigneron, J.-P. J. Heterocyclic Chem. 1990, 27, 1633.
20. Maffei, S.; Pietra, S.; Cattaneo, A. Gazz. Chim. Ital. 1953, 83, 327; Maffei, S.; Pietra, S.; Cattaneo, A. Gazz. Chim. Ital. 1953, 83, 812; Chernetskii, V.P.; Kiprianov, A.I. Ukrain. Khim. Zhur. 1955, 21, 367, C.A. 1955, 49, 14774.
21. Maffei, S.; Pietra, S.; Cattaneo, A. Gazz. Chim. Ital. 1953, 83, 327; Maffei, S.; Pietra, S.; Cattaneo, A. Gazz. Chim. Ital. 1953, 83, 812; Chernetskii, V.P.; Kiprianov, A.I. Ukrain. Khim. Zhur. 1955, 21, 367, C.A. 1955, 49, 14774.
22. Maffei, S.; Pietra, S.; Cattaneo, A. Gazz. Chim. Ital. 1953, 83, 327; Maffei, S.; Pietra, S.; Cattaneo, A. Gazz. Chim. Ital. 1953, 83, 812; Chernetskii, V.P.; Kiprianov, A.I. Ukrain. Khim. Zhur. 1955, 21, 367, C.A. 1955, 49, 14774.
23. Maffei, S.; Pietra, S.; Cattaneo, A. Gazz. Chim. Ital. 1953, 83, 327; Maffei, S.; Pietra, S.; Cattaneo, A. Gazz. Chim. Ital. 1953, 83, 812; Chernetskii, V.P.; Kiprianov, A.I. Ukrain. Khim. Zhur. 1955, 21, 367, C.A. 1955, 49, 14774.
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28. Ref. 1b, p. 184.
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31. SHELXTL, Siemens Analytical X-Ray Instruments, Madison, WI.
32. 1H n.m.r. spectra for crude and crystalline products were recorded showing negligible differences.
33. The preparation of products 4c and 7 was carried out at 80°C for 1.5 h.