Modified Methods for the Synthesis of Carbazole from Phenothiazine
Abstract
:Introduction
Results and Discussion
Conclusions
Acknowledgments
Experimental
General
Carbazole (2) using Lithium
Carbazole using Lithium and PPh3
Carbazole using Lithium and Sodium
References and Notes
- Cadogan, J.I.G.; Done, J.N.; Lunn, G. Nitrene-induced Cyclisations Accompanied by Rearrangement in Thermolyses of Aryl 2-Azidophenyl Sulphones. J. Chem. Soc., Perkin Trans.1 1976, 16, 1749–1757. [Google Scholar] Cadogan, J.I.G.; Kulik, S.; Thomson, C.; Todd, M.J. A New Synthesis of Phenothiazines involving a New Molecular Rearrangement. J. Chem. Soc. (C) 1970, 2437–2444. [Google Scholar] Cadogan, J.I.G.; Kulik, S. The ‘ Blocked ortho ’ Effect in Reactions of 2,6-Di-substituted Aryl 2-Nitrophenyl and 2,6-Di-substituted Aryl 2-Azidophenyl Sulfides. J. Chem. Soc. (C) 1971, 2621–2632. [Google Scholar]
- Becker, S.; Fort, Y.; Vanderesse, R.; Caubere, P. Activation of Reducing Agents. Sodium Hydride Containing Complex Reducing Agents. J. Org. Chem. 1989, 54, 4848–4853. [Google Scholar] Gilman, H.; Honeycutt, J.B.; Ingham, R.K. Cleavage Studies in the Carbazole and Phenothiazine Systems. J. Am. Chem. Soc. 1957, 22, 338–339. [Google Scholar] Back, T.G.; Yang, K. Desulphurization of Benzothiophene Derivatives with Nickel Boride. J. Chem. Soc., Chem. Commun. 1990, 11, 819–820. [Google Scholar]
- Eisch, J.J.; Kyoung, R. Hydrodesulfurization and Ring Contraction of Sulfur Heterocycles by Nickel (0) Complexes. J. Organomet. Chem. 1977, 139, C51–C55. [Google Scholar] Eisch, J.J.; Hallenbeck, L.E.; Han, K.I. Hydrodesulfurization of Organosulfur Heterocycles by Metal Hydride-Nickel (0) Complexes. J. Am. Chem. Soc. 1986, 108, 7763–7767. [Google Scholar] Klingstedt, T.; Hallberg, A.; Dunbar, P.; Martin, A. Preparation of Pyrrolo[3,2,1-jk]carbazole by Nickel(0) Mediated Ring Contraction of Pyrrolo[3,2,1-kl]phenothiazine. Proton NMR and Mass Spectral Studies. J. Heterocycl. Chem. 1985, 22, 1547–1550. [Google Scholar]
- Ris, C. Ueber das Thio-β-dinaphtylamin and einige Derivate desselben. Ber. Dtsch. Chem. Ges. 1886, 19, 2240–2246. [Google Scholar] Goske, A. Carbazol aus Thiodiphenylamin. Ber. Dtsch. Chem. Ges. 1887, 20, 232–234. [Google Scholar] Lin, D.C.K.; Thomson, M.L.; DeJongh, D.C. Effect of the N-Phenyl Substituent on the Pyrolyses of 1-Phenyl-2-benzothiazolinone and 1-Phenyl-2-benzothiazolinethione. Can. J. Chem. 1975, 53, 2293–2299. [Google Scholar]
- Gilman, H.; Dietrich, J.J. Lithium Cleavages of Some Heterocycles in Tetrahydrofuran. J. Am. Chem. Soc. 1958, 80, 380–383. [Google Scholar] [CrossRef]
- Lieber, E.; Somasekhara, S. 7-Dibenzo [c, g] Carbazole by Lithium Desulphurisation of 7-Dibenzo [c, h] Phenothiazine. Chem. Ind. (London) 1958, 1367–1368. [Google Scholar]
- Gilman, H.; Dietrich, J.J. Lithium Cleavages of some Heterocycles in Tetrahydrofuran. J. Org. Chem. 1957, 22, 851–853. [Google Scholar] [CrossRef]
- Sample Availability: Not availabl.
© 2001 by MDPI (http://www.mdpi.org). Reproduction is permitted for noncommercial purposes.
Share and Cite
Miller, R.B.; Farmer, S.C. Modified Methods for the Synthesis of Carbazole from Phenothiazine. Molecules 2001, 6, 668-672. https://doi.org/10.3390/60800668
Miller RB, Farmer SC. Modified Methods for the Synthesis of Carbazole from Phenothiazine. Molecules. 2001; 6(8):668-672. https://doi.org/10.3390/60800668
Chicago/Turabian StyleMiller, R. Bryan, and Steven C. Farmer. 2001. "Modified Methods for the Synthesis of Carbazole from Phenothiazine" Molecules 6, no. 8: 668-672. https://doi.org/10.3390/60800668