Abstract
This review presents a systematic and comprehensive survey of the method of preparation and the chemical reactivity of 2-acetylphenothiazines. The target compounds are important intermediates for the synthesis of a variety of synthetically useful and novel heterocyclic systems with different ring sizes such as isoxazole, pyrazole, pyrimidine, pyridine, quinolone, pyrazolo[3,4-d] pyridazine, 1,5-benzothiazepine, and triazolo[1,5-a] pyridine.
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S.R. Tilak, R. Tyagi, B. Goel, K.K. Saxena, Indian Drugs 35, 221–226 (1998)
V.G. Garcia, M. Longo, J.E.C. Gualberto, A.F. Bosco, M.J. Nagata, E. Ervolino, L.H. Theodoro, J. Periodontal Res. 49, 584–594 (2014)
M. Viveros, L.D. Amaral, Int. J. Antimicrob. Agents 17, 225–228 (2001)
N. Motohasho, M. Kawase, S. Saito, H. Sakagami, Curr. Drug Targets 1, 237–245 (2000)
D. Leancer, L.A. Mitscher, Org. Chem. Drug Synth. 1, 372–392 (1976)
S. Shweta, S.N. Pandeya, V. Anupam, Y. Deepika, IJRAP 2, 1130–1137 (2011)
A.S. Al-Bogami, A.E.M. Mekky, T.S. Saleh, Tetrahedron 69, 6787–6798 (2013)
G. Mehta, T. Sambaiah, B.G. Maiya, M. Sirish, A. Dattagupta, J. Chem. Soc. Perkin Trans. 1, 295 (1995)
Md.A.B.H. Susan, A. Ishibashi, Y. Takeoka, M. Watanabe, Biointerfaces 38, 167–173 (2004)
M. Mayer, P.T. Lang, S. Gerber, P.B. Madrid, I.G. Pinto, R.K. Guy, T.L. James, Chem. Biol. 13, 993 (2006)
G.A. Silva, L.M.M. Costa, F.C.F. Brito, A.L.P. Miranda, E.J. Barreiroa, C.A.M. Fraga, Bioorg. Med. Chem. 12, 3149 (2004)
N. Naik, H.V. Kumar, V. Veena, Der Pharma Lett 4, 786 (2012)
S.J. Lafta, Al-Mustansiriyah J. Sci. 23, 75 (2012)
M. Dawei, Q. Geng, H. Zhang, Y. Jiang, Angew. Chem. Int. Ed. 49, 1291 (2010)
P.B. Madrid, W.E. Polgar, L. Toll, M.J. Tanga, Bioorg. Med. Chem. 17, 3014 (2007)
A. Takada, H. Nishimura, Chem. Pharm. Bull. 10, 1 (1962)
G. Cauquil, A. Casadevall, Bull. Soc. Chim. Fr. 50, 768–781 (1955)
T. Hirata, J.S. Driscoll, J. Pharm. Sci. 65, 1699–1701 (1976)
C. Chan, H. Yin, J. Garforth, J.H. McKie, R. Jaouhari, P. Speers, K.T. Douglas, P.J. Rock, V. Yardley, S.L. Croft, A.H. Fairlamb, J. Med. Chem. 41, 148 (1998)
R. Baltzly, M. Harfenist, F.J. Webb, J. Am. Chem. Soc. 68, 2673 (1946)
S.P. Massie, I. Cooke, W.A. Hills, J. Org. Chem. 21, 1006 (1956)
J. Itier, A. Casadevall, Bull. Soc. Chim. Fr. 7, 2342 (1969)
A.N. Gritsenko, S.V. Zhuravlev, J. Gen. Chem. USSR 30, 2640 (1960)
S.S. Nikulin, V.M. Misin, V.M. Komarov, M.V. Misin, Russ. J. Appl. Chem. 76, 1327 (2003)
A. Burger, B.C. John, J. Org. Chem. 16, 1113 (1953)
S. Darvesh, R.S. McDonald, A. Penwell, S. Conrad, K.V. Darvesh, D. Mataija, G. Gomez, A. Caines, R. Walsh, E. Martin, Bioorg. Med. Chem. 13, 211 (2005)
S. Darvesh, R.S. McDonald, A. Penwell, S. Conrad, K.V. Darvesh, D. Mataija, G. Gomez, A. Caines, R. Walsh, E. Martin, Bioorg. Med. Chem. 15, 6367 (2007)
R. Dahlbom, B. Bjoerkqvist, Acta Chem. Scand. 15, 2043 (1961)
E. Profft, F. Kasper, Arzneimittelforschung 12, 48 (1962)
B.V. Kudryavtsev, D.K. Yarmukhametova, Bull. Acad. Sci. USSR Div. Chem. Sci. 19, 1583 (1970)
M. Schmidt, M. Teitge, M.E. Castillo, T. Brandt, B. Dobner, A. Langner, Arch. Pharm. 341, 624 (2008)
Immusol Incorporated, WO 2008/21745, (A2) English (2008)
A.W. Franz, R. Turdean, T.J.J. Mueller, Z. Zhou, A. Wagener, S. Ernst, W.R. Thiel, B. Sarkar, M. Hartmann, Eur. J. Org. Chem. 200, 3895 (2009)
S. Auvin, C. De Lassauniere, P. Etienne, US 2005/222045, (A1) English (2005)
J. Brem, S. Pilbák, C. Paizs, G. Bánóczi, F.-D. Irimie, M.-I. Toşa, L. Poppe, Tetrahedron Asymmetry 22, 916 (2011)
K. Kubota, H. Kurebayashi, H. Miyachi, M. Tobe, M. Onishi, Y. Isobe, Bioorg. Med. Chem. Lett. 19, 2766 (2009)
C. Bright, T.J. Brown, P. Cox, F. Halley, P. Lockey, I.M. McLay, U. Moore, B. Porter, R.J. Williams, Bioorg. Med. Chem. Lett. 8, 771 (1998)
J.W. Hulshof, H.F. Vischer, M.H.P. Verheij, S.A. Fratantoni, M.J. Smit, I.J.P. de Esch, R. Leurs, Bioorg. Med. Chem. 14, 7213 (2006)
A.N. Gritsenko, S.V. Zhuravlev, J. Gen. Chem. USSR (Engl. Transl.) 32, 1912 (1962)
M.J. Yu, J.R. McCowan, K.J. Thrasher, P.T. Keith, C.A. Luttman, P.P.K. Ho, R.D. Towner, B. Bertsch, J.S. Horng, J. Med. Chem. 35, 716 (1992)
T.N. Bansode, J.V. Shelke, V.G. Dongre, Eur. J. Med. Chem. 44, 5094 (2009)
C. Petry, M. Lang, H.A. Staab, H. Bauer, Angew. Chem. Int. Ed. Engl. 32, 1711 (1993)
H. Bauer, F. Stier, C. Petry, A. Knorr, C. Stadler, H.A. Staab, Eur. J. Org. Chem. 17, 3255 (2001)
T.W. Kwon, A.P. Kulkarni, S.A. Jenekhe, Synth. Met. 158, 292 (2008)
R.F. Boswell Jr., R.L. Duncan Jr., J. Funderburk, W.J. Welstead Jr., J. Med. Chem. 21, 136 (1978)
P. Kumar, C. Nath, J.C. Agarwal, C. Jagdish, K.P. Bhargava, K. Shanker, J. Indian Chem. Sec. B Org. Inc. Med. Chem. 22, 952 (1983)
M. Fujimoto, Bull. Chem. Soc. Jpn 32, 480 (1959)
H. S. Margaret, Bloomfield and S. Nathan, Schering Corp., US 2887481 (1957)
A.N. Gritsenko, S.V. Zhuravlev, J. Gen. Chem. USSR (Engl. Transl.) 33, 3628 (1963)
H.-C. Chiu, Y.-R. Chen, S.-L. Yu, L.-J. Teng, S.-L. Lee, N. Kapuriya, D. Wang, S.K. Kulp, C.-S. Chen, Bioorg. Med. Chem. 20, 4653 (2012)
R.K. Upadhyay, S.U. Megha, S. Jain, Eur. J. Chem. 6, 254 (2009)
S.N. Sawhney, G.S. Dhendsa, V. Dharam, J. Indian Chem. Soc. 65, 643 (1988)
T.N. Bansode, G.A. Meshram, J. Heterocycl. Chem. 49, 1004 (2012)
H.H. Zoorob, W.S. Hamama, J. Metri, A. Zayed, Chem. Scr. 18, 206 (1981)
G. Vanangamudi, K. Ranganathan, G. Thirunarayanan, World J. Chem. 7, 22 (2012)
A.V. Saranya, S. Ravi, Res. J. Recent Sci. 1, 40 (2012)
F.D. Popp, J. Heterocycl. Chem. 19, 589 (1982)
V. Stepanenko, M. Jesus, W. Correa, I. Guzman, C. Vazquez, L. Ortiz, M. Ortiz-, Tetrahedron Asymmetry 18, 2738 (2007)
M. O. Marciales, V. Stepanenko, W. C. Ramirez, M. Jesus, US 2008/200672, (A1) English (2008)
L. Yang, S.A. Lang, J. Heterocycl. Chem. 14, 345 (1977)
R. Gompper, J. Hock, Synth. Met. 84, 339 (1997)
J.P. Raval, K.R. Desai, ARKIVOC xiii, 21 (2005)
K. Bajaj, V.K. Srivastavia, A. Kumar, Indian J. Chem. 43B, 157 (2004)
V.K. Salvi, S. Sharma, C. Sharma, D. Bhambi, G.L. Talesara, Indian J. Chem. 48B, 1583 (2009)
G. Dumitriu, A. Ghinet, E. Bîcu, B. Rigo, J. Dubois, A. Farce, D. Belei, Bioorg. Med. Chem. 24, 3180 (2014)
A.V. Saranya, S. Ravi, S. Venkatachalapathi, Res. J. Chem. Sci. 3, 82–85 (2013)
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Gouda, M.A., Hamama, W.S., Kamal El-din, H.A. et al. 2-Acetylphenothiazines as synthon in heterocyclic synthesis. Res Chem Intermed 42, 6143–6162 (2016). https://doi.org/10.1007/s11164-016-2450-x
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DOI: https://doi.org/10.1007/s11164-016-2450-x