Imidothiocarbonates. V. Preparations and Properties of Novel Azomethine Ylides and Thiocarbonyl Ylides from Sulfur-contained Heterocycles
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概要
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Preparations and properties of some novel azomethine ylides and thiocarbonyl ylides containing 1,3-dithiolanium moiety have been studied. Azomethine ylides, <B>3a</B>, <B>b</B>, and <B>c</B>, were prepared by deprotonation of 2-(<I>N</I>-methyl-<I>N</I>-phenacyl)amino-(<B>2a</B>), 2-(<I>N</I>-<I>p</I>-nitrobenzyl-<I>N</I>-methyl)amino-(<B>2b</B>), and 2-(<I>N</I>-carbethoxymethyl-<I>N</I>-methyl)amino-1,3-dithiolanium salt (<B>2c</B>), respectively. Azomethine ylides <B>3a</B>, <B>b</B> reacted with benzaldehydes to give 1,3-dipolar cycloadducts which are new class of spiro orthocarbonates, otherwise it is difficult to obtain. Elimination of ethylene sulfide from the spiro orthocarbonates easily occurred to give thiocarbonyl compounds. In the absence of dipolarophiles, <B>3a</B> cyclized intramolecularly to give 1,3-oxazoline-2-thione derivative. Formation of the thiocarbonyl ylides by deproptonation of 2-phenacylthio-1,3-oxazolium and 2-<I>p</I>-bromophenacylthio-1,3-dithiolanium salts, and their different cyclization to spiro compounds were also studied. Reaction of thiocarbonyl ylides <B>16</B> with <I>p</I>-nitrobenzaldehyde afforded <I>p</I>-nitrochalcone. Mechanisms of these interesting reactions and their synthetic utility were discussed.
- 公益社団法人 日本化学会の論文
著者
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Okawara Makoto
Research Laboratory Of Resources Utilization Tokyo Institute Of Technology
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Ueno Yoshio
Research Institute For Biosciences And Department Of Toxicology And Microbial Chemistry Faculty Of Pharmaceutical Sciences Science University Of Tokyo
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Ueno Yoshio
Research Laboratory of Resources Utilization, Tokyo Institute of Technology
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