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• Dudova, K
• Castek, F
• Machacek, V
• Simunek, P
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• Dudova, K
• Castek, F
• Machacek, V
• Simunek, P
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• Dudova, K
• Castek, F
• Machacek, V
• Simunek, P

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Molecules 2002, 7(1), 7-17; doi:10.3390/70100007

Article

Preparation of Substituted Methyl o-Nitrophenyl Sulfides

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

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

Download PDF Full-Text [101 KB, uploaded 2 October 2008 14:58 CEST]

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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