Abstract
An exclusive regioselective formation of 2-thiomethyl ether substituted isomer of the privileged nucleus of 1,5-benzodiazepines was achieved from the reaction of p-nitro-o-phenylenediamine with a variety of α-oxoketene dithioacetals derived from several active methylene compounds, by exploiting the strategy based on the variation of electrophilicity of the two electrophilic centers of α-oxoketene dithioacetals and the hard and soft nucleophilic profiles of the p-nitro substituted o-phenylenediamines.
An exclusive regioselective formation of 2-thiomethyl ether substituted isomer of the privileged nucleus of 1,5-benzodiazepines was achieved from the reaction of p-nitro-o-phenylenediamine with a variety of α-oxoketene dithioacetals derived from several active methylene compounds.
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References
Chadha S, Paul S and Kapoor K K 2011 J. Chem. Pharm. Res. 3(2) 331
Wang Z X and Qin H L 2005 J. Hetrocycl. Chem. 42(5) 1001
Wei X L, Min Z and Hua S W 2011 Chem. Res. Chinese Universities 27 228
Kuo C W, Wang C C, Kavala V and Yao C F 2008 Molecules 13(9) 2313
(a) Kumar R and Joshi Y C 2007 Arkivoc 13 142; (b) Kumar R and Joshi Y C 2008 J. Serb. Chem. Soc. 73(10) 937; (c) Parveen A, Patil V A, Baseer M A and Ahmed S K 2011 Int. J. Ind. Chem. 2(3) 144
Yadav K M, Mohanta P K, lla H and Junjappa H 1996 Tetrahedron 52 14049
Junjappa H, Ila H and Asokan C V 1990 Tetrahedron 46(16) 5423
Mang W, Shao-Gaung S and Qun L 2004 Synth. Commun. 34(2) 287
(a) Ali S M and Tanimoto S 1990 Bull. Inst. Chem. Res. 68(3) 199; (b) Marino J P and Kostusyk J L 1979 Tetrahedron Lett. 20(27) 2489; (c) Chauhan S M S and Junjappa H 1976 Tetrahedron 32(14) 1779
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Authors are thankful to the Punjab University, Chandigarh for providing the spectral data of the compounds.
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CHAUDHARY, P., GUPTA, A., DEVI, P. et al. Hard and soft electrophilic and nucleophilic dissymmetry of α-oxoketenedithioacetals and p-nitro-o-phenylenediamine exploited to achieve the regioselectivity in the synthesis of 2-thiomethyl ether substituted isomer of the privileged nucleus of 1,5-benzodiazepines over to its 4-substituted isomers. J Chem Sci 125, 1487–1491 (2013). https://doi.org/10.1007/s12039-013-0520-9
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DOI: https://doi.org/10.1007/s12039-013-0520-9