Tele nucleophilic aromatic substitutions in 1-nitro-3-and 1,3-dinitro-5-trichloromethylbenzene, and 3-trichloromethylbenzonitrile. A new synthesis of the 1,4-benzothiazine-3(4H)-one ring system from 3-nitrobenzoic acid

 
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2000 (EN)
Tele nucleophilic aromatic substitutions in 1-nitro-3-and 1,3-dinitro-5-trichloromethylbenzene, and 3-trichloromethylbenzonitrile. A new synthesis of the 1,4-benzothiazine-3(4H)-one ring system from 3-nitrobenzoic acid (EN)

Giannopoulos, T. (EN)

Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας (EL)
Giannopoulos, T. (EN)

3-Trichloromethylnitrobenzene 2, 1,3-dinitro-5-trichloromethylbenzene 13 and 3-trichloromethylbenzonitrile 18 react with sodium methoxide to give 4-methoxy-3-nitrobenzaldehyde 6, 4-methoxy-3,5-dinitrobenzaldehyde 15 and 5-dimethoxymethyl-2-methoxybenzonitrile 19, respectively. Compounds 2 and 13 react with methyl thioglycolate to afford dichloromethylacetates 7 and 16, respectively. These products are the result of tele nucleophilic aromatic substitution. Compound 18 reacted with methyl thioglycolate to give acetate 20 resulting from nucleophilic displacement of cyanide. Reductive cyclisation of 7 afforded benzothiazine 11. (C) 2000 Elsevier Science Ltd. All rights reserved. (EN)

benzenes (EN)

Πανεπιστήμιο Ιωαννίνων (EL)
University of Ioannina (EN)

Tetrahedron (EN)

English

2000

<Go to ISI>://000084896900014

Elsevier (EN)



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