The reactions of 2-arylacetylene-1-sulfonamides with heterocumulenes.
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概要
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The syntheses of new heterocyclic compounds by the reaction of 2-arylacetylene-1-sulfonamides <B>1</B>, (<I>Z</I>)-β-bromo- <B>12</B> or (<I>Z</I>)-α-chloro-β-styrenesulfonamides <B>13</B> with heterocumulenes are described. Weak base treatment of ureas R<SUP>1</SUP>C<SUB>6</SUB>H<SUB>4</SUB>C≡CSO<SUB>2</SUB>NHC(=O)NHR<SUP>2</SUP> prepared from <B>1</B> and isocyanates gave 2-amino-6-aryl-1,4,3-oxathiazine 4,4-dioxides, whereas strong base treatment of the ureas afforded 3-oxo-4,5-diphenyl-2,3-dihydro-1,2,4-thiadiazine 1,1-dioxides where R<SUP>2</SUP> is a phenyl group. The thiadiazines were also prepared by the strong base treatment of <I>N</I>-((<I>Z</I>)-α-bromo- or (<I>Z</I>)-β-chlorostyrylsulfonyl)-<I>N</I>′-phenylureas. The reaction of <B>1</B>,<B>12</B>, or <B>13</B> with isothiocyanates in the presence of weak base gave 3-amino-5-aryl-1,4,2-dithiazine 1,1-dioxides, but the major products produced were 3-amino-5-benzylidene-1,4,2-dithiazole 1,1-dioxides when <B>12a</B> was treated with isothiocyanates in the presence of strong base. The reaction of <B>1</B> with carbon disulfide and dimethyl sulfate in the presence of 5 M NaOH afforded 3-methylthio-5-benzylidene-1,4,2-dithiazole 1,1-dioxide with a small amount of 3-methylthio-5-aryl-1,4,2-dithiazine 1,1-dioxide. A mixture of both isomers was also prepared from <B>12a</B>. Possible mechanisms for the formation of the heterocycles from <B>1</B>, <B>12</B>, or <B>13</B> are suggested.
- 公益社団法人 日本化学会の論文
著者
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Hasegawa Kiyoshi
Department Of Applied Chemistry Faculty Of Engineering Toyama University
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Hirooka Syuzi
Department Of Applied Chemistry. Faculty Of Engineering Toyama University
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Kawahara Hiroshi
Department Of Dental Anesthesiology Kyushu Dental College
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NAKAYAMA AKIHIKO
Department of Obstetrics and Gynecology, and Department of Pharmacology, School of Medicine
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Ishikawa Keiichi
Department of Industrial Chemistry, Faculty of Engineering, Toyama University
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Takeda Nobuyuki
Department of Industrial Chemistry, Faculty of Engineering, Toyama University
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Mukai Hisakatsu
Department of Industrial Chemistry, Faculty of Engineering, Toyama University
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Takeda Nobuyuki
Department of Applied Chemistry, Kogakuin University
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