Preparation of Substituted Methyl o-Nitrophenyl Sulfides

Molecules

Katerina Dudova¹  Frantisek Castek²  Vladimir Machacek¹ 

[1] id="af1-molecules-07-00007">Department of Organic Chemistry, University of Pardubice, Čs. legií 565, 532 10 Pardubice, Czech. Republic, Tel. [phone], Fax [phone]

关键词: Nucleophilic aromatic substitution;    sulfur nucleophiles;    ring closure;   

DOI  :  10.3390/70100007

来源: mdpi

【 摘 要 】

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).

【 授权许可】

Unknown   
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