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1. Preparation of Substituted Methyl o-Nitrophenyl Sulfides

Author

Petr Simunek, Vladimir Machacek, Frantisek Castek, and Katerina Dudova

Subjects
Nucleophilic aromatic substitution, sulfur nucleophiles, ring closure, Organic chemistry, QD241-441
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).

Published
2002
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2. Preparation of Substituted Methyl o-Nitrophenyl Sulfides

Author

Frantisek Castek, Katerina Dudova, Petr Simunek, and Vladimír Macháček

Subjects
Base (chemistry), Pharmaceutical Science, ring closure, Ring (chemistry), Medicinal chemistry, Article, Analytical Chemistry, lcsh:QD241-441, chemistry.chemical_compound, lcsh:Organic chemistry, Nucleophilic aromatic substitution, Drug Discovery, Pyridine, Nucleophilic substitution, Organic chemistry, Physical and Theoretical Chemistry, Triethylamine, Carbanion, sulfur nucleophiles, chemistry.chemical_classification, Organic Chemistry, chemistry, Chemistry (miscellaneous), Nitro, Molecular Medicine
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-dinitro-benzo[b]thiophene-2-carboxylate (11).

Published
2002

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