Synthesis and reaction of 6‐substituted 3‐methoxycarbonyl‐4‐methylthio‐2H‐pyran‐2‐one derivatives
Synthesis and reaction of 6‐substituted 3‐methoxycarbonyl‐4‐methylthio‐2H‐pyran‐2‐one derivatives
复制标题
6-取代3-甲氧基羰基-4-甲硫基-2H-吡喃-2-酮衍生物的合成与反应
DOI：
10.1002/jhet.5570240612
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发表时间：
1987
期刊：
影响因子：
--
通讯作者：
Y. Matsuda
中科院分区：
文献类型：
--
作者：
Y. Tominaga;A. Ushirogochi;Y. Matsuda
芳基和苯乙烯基甲基酮1a-m与二甲基双（甲硫基）亚甲基丙二酸酯（2）在氢氧化钾存在下在二甲基亚砜中反应得到相应的6-芳基-和6-苯乙烯基-4-甲硫基-2-氧代-2H-吡喃-3-羧酸甲酯3a-m。6-芳基衍生物3a-d，g用甲醇钠在甲醇中处理，得到相应的6-芳基-4-甲氧基-2H-吡喃-2-酮8a-dand 9。以6-芳基-4-甲硫基-2H-吡喃-2-酮4a，b为原料进行脱硫反应，合成了6-芳基-4-甲硫基-2H-吡喃-2-酮4a，b;以6-芳基-4-甲硫基-2H-吡喃-2-酮3g为原料进行脱硫反应，合成了氨基苯甲酸（8 e）;以过氧化氢或3-氯过氧苯甲酸处理3，得到了相应的4-甲基亚磺酰基-2H-吡喃-2-酮10a-fin。还描述了10a-f与亲核试剂的置换反应。
Reaction of aryl and styryl methyl ketones1a‐mwith dimethyl bis(methylthio)methylenemalonate (2) in the presence of potassium hydroxide in dimethyl sulfoxide gave the corresponding methyl 6‐aryl‐ and 6‐styryl‐4‐methylthio‐2‐oxo‐2H‐pyran‐3‐carboxylates3a‐m.6‐Aryl derivatives3a‐d,gwere treated with sodium methoxide in methanol to give the corresponding 6‐aryl‐4‐methoxy‐2H‐pyran‐2‐ones8a‐dand9.Phenylcoumalin (7a) and paracotoin (7b) were synthesized by the desulfurization of 6‐aryl‐4‐methylthio‐2H‐pyran‐2‐ones4a,b.Similarly, anibine (8e) was also synthesized from3g.Treatment of3with hydrogen peroxide or 3‐chloroperoxybenzoic acid gave the corresponding 4‐methylsulfiny‐2H‐pyran‐2‐ones10a‐fin good yields. Displacement reactions of10a‐fwith nucleophilic reagents are also described.