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Synthesis of New Derivatives of 1-Azaphenothiazine via Buchwald-Hartwig Amination Methodology
Corresponding Author(s) : D.I. Ugwu
Asian Journal of Chemistry,
Vol. 27 No. 4 (2015): Vol 27 Issue 4
Abstract
Synthesis of new derivatives of 1-azaphenothiazine (10a-d) via tandem amination methodology is reported. This was achieved by the reaction of 2-aminothiophenol (6) with 2,3,5-trichloropyridine (7) in aqueous basic medium to yield 3-chloro-1-azaphenothiazine (8) as a greenish yellow solid. Compound 8 was then subjected to palladium catalyzed Buchwald-Hartwig coupling reaction with substituted amines (9a-d), by refluxing using palladium acetate [Pd(OAc)2] as palladium source catalyst, potassium carbonate as base, 1,4-bis(2-hydroxy-3,5-ditert-butylbenzyl)piperazine as ligand and tert-butanol (t-BuOH) as solvent at 110 °C to yield 3-anilino-1-azaphenothiazine derivatives (10a-d) in good to excellent yield. The compounds were characterised using UV, FTIR, 1H NMR, 13C NMR spectroscopy and elemental analysis.
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- S.P. Massie, Chem. Rev., 54, 797 (1954); doi:10.1021/cr60171a003.
- N.L. Smith, J. Org. Chem., 16, 415 (1951); doi:10.1021/jo01143a011.
- U.C. Okoro, Indian J. Chem., 29B, 117 (1990).
- C.O. Okafor, Int. J. Sulphur Chem., 6, 237 (1971).
- C.O. Okafor, J. Heterocycl. Chem., 18, 405 (1981); doi:10.1002/jhet.5570180235.
- A.N. Gritsenko, Z.I. Ermakova, T.Y. Mozhaeva, V.S. Troitskay and S.V. Zhuravlev, Chem. Abstr., 83, 9942 (1975).
- V.A. Petrow and E.L. Rewald, J. Chem. Soc., 40, 591 (1945); doi:10.1039/jr9450000591.
- C.O. Okafor, I.O. Uche and L.E.S. Akpanisi, J. Heterocycl. Chem., 18, 1589 (1981); doi:10.1002/jhet.5570180820.
- C.O. Okafor, M.L. Steenberg and J.P. Buckley, Eur. J. Med. Chem., 3, 249 (1976).
- C.O. Okafor, J. Org. Chem., 40, 2753 (1975); doi:10.1021/jo00907a010.
- D.S. Surry and S.L. Buchwald, Chem. Sci., 2, 27 (2010); doi:10.1039/c0sc00331j.
- J.F. Hartwig, Angew. Chem. Int. Ed., 37, 2046 (1998); doi:10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO;2-L.
- J.P. Wolfe, S. Wagaw, J.F. Marcoux and S.L. Buchwald, Acc. Chem. Res., 31, 805 (1998); doi:10.1021/ar9600650.
- B. Schlummer and U. Scholz, Adv. Synth. Catal., 346, 1599 (2004); doi:10.1002/adsc.200404216.
- L. Jiang and S.L. Buchwald, in eds.: A. de Meijere and F. Diederich, Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH: Weinheim, Germany, p. 23 (1998).
- B.P. Fors, P. Krattiger, E. Strieter and S.L. Buchwald, Org. Lett., 10, 3505 (2008); doi:10.1021/ol801285g.
- B.P. Fors and S.L. Buchwald, J. Am. Chem. Soc., 132, 15914 (2010); doi:10.1021/ja108074t.
- B.P. Fors, D.A. Watson, M.R. Biscoe and S.L. Buchwald, J. Am. Chem. Soc., 130, 13552 (2008); doi:10.1021/ja8055358.
- D. Zim and S.L. Buchwald, Org. Lett., 5, 2413 (2003); doi:10.1021/ol034561h.
- 20 G.D. Vo and J.F. Hartwig, J. Am. Chem. Soc., 131, 11049 (2009); doi:10.1021/ja903049z.
- C.O. Okafor, J. Org. Chem., 38, 4386 (1973); doi:10.1021/jo00965a008.
- K. Venkataraman, Chem. Synth. Dyes, 11,791 (1952).
- C.O. Okafor, J. Org. Chem., 40, 2753 (1975); doi:10.1021/jo00907a010.
- D.S. Wise Jr. and R.N. Castle, J. Heterocycl. Chem., 11, 1001 (1974); doi:10.1002/jhet.5570110627.
- J. Karpinska, B. Starczewska and H. Puzanowska-Tarasiewicz, Anal. Sci., 12, 161 (1996); doi:10.2116/analsci.12.161.
References
S.P. Massie, Chem. Rev., 54, 797 (1954); doi:10.1021/cr60171a003.
N.L. Smith, J. Org. Chem., 16, 415 (1951); doi:10.1021/jo01143a011.
U.C. Okoro, Indian J. Chem., 29B, 117 (1990).
C.O. Okafor, Int. J. Sulphur Chem., 6, 237 (1971).
C.O. Okafor, J. Heterocycl. Chem., 18, 405 (1981); doi:10.1002/jhet.5570180235.
A.N. Gritsenko, Z.I. Ermakova, T.Y. Mozhaeva, V.S. Troitskay and S.V. Zhuravlev, Chem. Abstr., 83, 9942 (1975).
V.A. Petrow and E.L. Rewald, J. Chem. Soc., 40, 591 (1945); doi:10.1039/jr9450000591.
C.O. Okafor, I.O. Uche and L.E.S. Akpanisi, J. Heterocycl. Chem., 18, 1589 (1981); doi:10.1002/jhet.5570180820.
C.O. Okafor, M.L. Steenberg and J.P. Buckley, Eur. J. Med. Chem., 3, 249 (1976).
C.O. Okafor, J. Org. Chem., 40, 2753 (1975); doi:10.1021/jo00907a010.
D.S. Surry and S.L. Buchwald, Chem. Sci., 2, 27 (2010); doi:10.1039/c0sc00331j.
J.F. Hartwig, Angew. Chem. Int. Ed., 37, 2046 (1998); doi:10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO;2-L.
J.P. Wolfe, S. Wagaw, J.F. Marcoux and S.L. Buchwald, Acc. Chem. Res., 31, 805 (1998); doi:10.1021/ar9600650.
B. Schlummer and U. Scholz, Adv. Synth. Catal., 346, 1599 (2004); doi:10.1002/adsc.200404216.
L. Jiang and S.L. Buchwald, in eds.: A. de Meijere and F. Diederich, Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH: Weinheim, Germany, p. 23 (1998).
B.P. Fors, P. Krattiger, E. Strieter and S.L. Buchwald, Org. Lett., 10, 3505 (2008); doi:10.1021/ol801285g.
B.P. Fors and S.L. Buchwald, J. Am. Chem. Soc., 132, 15914 (2010); doi:10.1021/ja108074t.
B.P. Fors, D.A. Watson, M.R. Biscoe and S.L. Buchwald, J. Am. Chem. Soc., 130, 13552 (2008); doi:10.1021/ja8055358.
D. Zim and S.L. Buchwald, Org. Lett., 5, 2413 (2003); doi:10.1021/ol034561h.
20 G.D. Vo and J.F. Hartwig, J. Am. Chem. Soc., 131, 11049 (2009); doi:10.1021/ja903049z.
C.O. Okafor, J. Org. Chem., 38, 4386 (1973); doi:10.1021/jo00965a008.
K. Venkataraman, Chem. Synth. Dyes, 11,791 (1952).
C.O. Okafor, J. Org. Chem., 40, 2753 (1975); doi:10.1021/jo00907a010.
D.S. Wise Jr. and R.N. Castle, J. Heterocycl. Chem., 11, 1001 (1974); doi:10.1002/jhet.5570110627.
J. Karpinska, B. Starczewska and H. Puzanowska-Tarasiewicz, Anal. Sci., 12, 161 (1996); doi:10.2116/analsci.12.161.