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Preparation of Substituted Methyl o-Nitrophenyl Sulfides
Department of Organic Chemistry, University of Pardubice, Čs. legií 565, 532 10 Pardubice, Czech Republic
* Author to whom correspondence should be addressed.
Received: 27 September 2001; in revised form: 9 November 2001 / Accepted: 13 November 2001 / Published: 31 January 2002
Abstract: The nucleophilic substitution of substituted o-nitrochlorobenzenes with substituted methanethiolates, catalysed with triethylamine or pyridine, has been used to prepare a series of appropriately substituted methyl-o-nitrophenylsulfides. The prepared compounds were identified by their 1H- and 13C-NMR spectra. The base catalysed ring closure of methyl 2-(methoxycarbonylmethylsulfanyl)-3,5-dinitrobenzenecarboxylate only results in an attack of carbanion on the ester group, not on a nitro group as with the other compounds prepared. The cyclisation product is methyl 3-hydroxy-5,7-dinitrobenzo[b]thiophene-2-carboxylate (11).
Keywords: Nucleophilic aromatic substitution; sulfur nucleophiles; ring closure
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Dudova, K.; Castek, F.; Machacek, V.; Simunek, P. Preparation of Substituted Methyl o-Nitrophenyl Sulfides. Molecules 2002, 7, 7-17.
Dudova K, Castek F, Machacek V, Simunek P. Preparation of Substituted Methyl o-Nitrophenyl Sulfides. Molecules. 2002; 7(1):7-17.
Dudova, Katerina; Castek, Frantisek; Machacek, Vladimir; Simunek, Petr. 2002. "Preparation of Substituted Methyl o-Nitrophenyl Sulfides." Molecules 7, no. 1: 7-17.