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Synthesis of 2,3-Dihydro-1H-benzo[b][1,4]diazepines with Aromatic Diamines and Acetonedicarboxylic Acid
Corresponding Author(s) : Juhyun Song
Asian Journal of Chemistry,
Vol. 26 No. 16 (2014): Vol 26 Issue 16
Abstract
2,3-Dihydro-1H-benzo[b][1,4]diazepines were obtained by the reaction of the corresponding diamines and acetonedicarboxylic acid in various methods. A plausible mechanism for the formation of 1,5-benzodiazepine is also discussed.
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- H. Schutz, Benzodiazepines; Springer: Heidelberg (1982); R.K. Smalley, in eds.: D. Barton and W.D. Ollis, Comprehensive Organic Chemistry; Pergamon: Oxford, Vol. 4, pp. 600 (1979).
- J.K. Landquist, in eds.: A.R. Katritzky and C.W. Rees, Comprehensive Heterocyclic Chemistry; Pergamon: Oxford, Vol. 1, p. 166, 170 (1984).
- L.H. Sternbach, Angew. Chem. Int. Ed. Engl., 10, 34 (1971); doi:10.1002/anie.197100341.
- M.C. Aversa, A. Ferlazzo, P. Giannetto and F.H. Kohnke, Synthesis, 230 (1986); doi:10.1055/s-1986-31628.
- A. Chimirri, S. Grasso, R. Ottana, G. Romeo and M.J. Zappala, Heterocycl. Chem., 27, 371 (1990); doi:10.1002/jhet.5570270250.
- W. Ried and E. Torinus, Chem. Ber., 92, 2902 (1959); doi:10.1002/cber.19590921138.
- J.A.L. Herbet and H. Suschitzky, J. Chem. Soc., Perkin Trans. 1, 2657 (1974); doi:10.1039/P19740002657.
- R. Contreras, H. R. Morales and A. Bulbarela, Heterocycles, 24, 135 (1986); doi:10.3987/R-1986-01-0135.
- J. Dai-Il, C. Tae-wonchoi, K. Yun-Young, K. In-Shik, P. You-Mi, L. Yong-Gyun and J. Doo-Hee, Synth. Commun., 29, 1941 (1999); doi:10.1080/00397919908086183.
- J.R. Merchant and D.S. Chotia, Indian J. Chem., 8, 814 (1975).
- S. Patai, M. Bentov and M.E. Reichmann, J. Am. Chem. Soc., 74, 845 (1952); doi:10.1021/ja01123a523.
- N. Kalyanam and S.G. Manjunatha, Indian J. Chem., 9, 892 (1991).
References
H. Schutz, Benzodiazepines; Springer: Heidelberg (1982); R.K. Smalley, in eds.: D. Barton and W.D. Ollis, Comprehensive Organic Chemistry; Pergamon: Oxford, Vol. 4, pp. 600 (1979).
J.K. Landquist, in eds.: A.R. Katritzky and C.W. Rees, Comprehensive Heterocyclic Chemistry; Pergamon: Oxford, Vol. 1, p. 166, 170 (1984).
L.H. Sternbach, Angew. Chem. Int. Ed. Engl., 10, 34 (1971); doi:10.1002/anie.197100341.
M.C. Aversa, A. Ferlazzo, P. Giannetto and F.H. Kohnke, Synthesis, 230 (1986); doi:10.1055/s-1986-31628.
A. Chimirri, S. Grasso, R. Ottana, G. Romeo and M.J. Zappala, Heterocycl. Chem., 27, 371 (1990); doi:10.1002/jhet.5570270250.
W. Ried and E. Torinus, Chem. Ber., 92, 2902 (1959); doi:10.1002/cber.19590921138.
J.A.L. Herbet and H. Suschitzky, J. Chem. Soc., Perkin Trans. 1, 2657 (1974); doi:10.1039/P19740002657.
R. Contreras, H. R. Morales and A. Bulbarela, Heterocycles, 24, 135 (1986); doi:10.3987/R-1986-01-0135.
J. Dai-Il, C. Tae-wonchoi, K. Yun-Young, K. In-Shik, P. You-Mi, L. Yong-Gyun and J. Doo-Hee, Synth. Commun., 29, 1941 (1999); doi:10.1080/00397919908086183.
J.R. Merchant and D.S. Chotia, Indian J. Chem., 8, 814 (1975).
S. Patai, M. Bentov and M.E. Reichmann, J. Am. Chem. Soc., 74, 845 (1952); doi:10.1021/ja01123a523.
N. Kalyanam and S.G. Manjunatha, Indian J. Chem., 9, 892 (1991).