Thiocyanation of N-arenesulfonyl-N′-aroyl-1,4-benzoquinone diimines

被引：0
|
作者：
S. A. Konovalova
A. P. Avdeenko
V. V. Pirozhenko
S. A. Goncharova
O. V. Shishkin
G. V. Palamarchuk
机构：
[1] Donbass State Engineering Academy,Institute of Organic Chemistry
[2] National Academy of Sciences of Ukraine,Institute for Single Crystals
[3] National Academy of Sciences of Ukraine,undefined
[4] Karazin Kharkiv National University,undefined
来源：
Russian Journal of Organic Chemistry | 2014年 / 50卷
关键词：
Potassium Thiocyanate; Quinoid Ring; Benzoquinone Imine; Methylbenzamide; Arenesulfonic Acid;
D O I：
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中图分类号：
学科分类号：
摘要：
The reaction of N-arenesulfonyl-N′-aroyl-1,4-benzoquinone diimines with potassium thiocyanate in glacial acetic acid occurs as 1,4-addition of thiocyanate ion by the sulfur atom to the quinoid ring in the meta position with respect to the aroyl group. The addition products, N-[4-(arenesulfonamido)-3-thiocyanatophenyl]-benzamides, partially undergo intramolecular cyclization to N-(2-imino-3-arenesulfonyl-2,3-dihydro-1,3-benzothiazol-6-yl)benzamides whose hydrolysis yields 2-amino-6-benzamido-1,3-benzothiazol-3-ium arenesulfonates. The latter lose arenesulfonic acid with formation of N-(2-amino-1,3-benzothiazol-6-yl)benzamides on treatment with a mixture of methanol with water and acetic acid.
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页码：1465 / 1471
页数：6
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