著者
長尾 善光 萩原 裕一 山田 省三 落合 正仁 藤田 榮一
出版者
The Pharmaceutical Society of Japan
雑誌
Chemical and Pharmaceutical Bulletin (ISSN:00092363)
巻号頁・発行日
vol.32, no.11, pp.4686-4689, 1984-11-25 (Released:2008-03-31)
参考文献数
15
被引用文献数
3 4

As a new extention of monitored aminolysis of 3-acyl-1, 3-thiazolidine-2-thione (ATT), a convenient procedure for the synthesis of αβ-unsaturated carboxylic acid amides has been developed using a new hetero-bifunctional reagent, 3-dimethylphosphonoacetyl-1, 3-thiazolidine-2-thione (DMPATT). DMPATT was effectively used as the bridging reagent between amino (or imino) compounds and aldehydes (or ketone) to afford various olefinic amides in good yields.
著者
小川 和男 山田 省三 寺田 忠史 山崎 富生 本邦 隆次
出版者
The Pharmaceutical Society of Japan
雑誌
Chemical and Pharmaceutical Bulletin (ISSN:00092363)
巻号頁・発行日
vol.33, no.6, pp.2256-2265, 1985-06-25 (Released:2008-03-31)
参考文献数
21
被引用文献数
1 6

2-Aklylidene-4-arylidene-1, 3-oxathiolan-5-one (III-1a-m) and 2, 4-diarylidene-1, 3-oxathiolan-5-one (III-2a-i) derivatives were synthesized by treating β-aryl-α-mercaptoacrylic acids (I) with alkanoic acid anhydrides (II) or by treating α-acylthio-β-arylacrylic acids (V) with thionyl chloride in dimethylformamide. Basic hydrolysis and methanolysis of III-1 and III-2 in the presence of lithium hydroxide easily occurred to give the corresponding ring-cleaved products, the carboxylic acid (I and II) and the ester (VII and VIII), respectively. The catalytic hydrogenation of the two olefinic bonds of III-2 in the presence of 10% palladium charcoal proceeded easily without ring cleavage to give 1, 3-oxathiolan-5-one (IXa-e) derivatives. The oxidation of III-1 and III-2 with m-chloroperbenzoic acid afforded the corresponding 1, 3-oxathiolan-5-one S-oxide (Xa, b) derivatives.