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Reactions of 4-chloro-5h-1,2,3-dithiazole-5-thione with α,β-unsaturated β-amino esters: Formation of 2-[2-(1-alkenylsulfanyl-1-alkoxycarbonyl-2-amino)-1,2-dicyano-vinylsulfanyl]-3-amino-2-alkenoic alkyl esters
✍ Scribed by Yong-Goo Chang; Kyongtae Kim; Yung Ja Park
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 2002
- Tongue
- English
- Weight
- 97 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
Treatment of 4‐chloro‐5__H__‐1,2,3‐dithiazole‐5‐thione with alkyl 3‐alkyl (or aryl)‐3‐amino‐2‐propenoates in the presence of pyridine (2 equivalents) in dichloromethane at reflux gave 2‐[2‐(1‐alkenylsulfanyl‐1‐alkoxy‐carbonyl‐2‐amino)‐1,2‐dicyanovinylsulfanyl]‐4 and‐1,2‐dicyanovinyldisulfanyl]‐3‐amino‐2‐alkenoic alkyl esters 7 in 16 to 60% and 8 to 48% yields, respectively.
📜 SIMILAR VOLUMES
Treatment of 4-chloro-5H-1,2,3-dithiazol-5-one with 3-alkyl (or aryl)-3-amino-2-propenoate esters in DMSO at 1200C gave the corresponding 2-thiocyanated esters 4 (major) and 5-alkoxycarbonyl-4-alkyl (or aryl)-4-thiazolin-2-ones 5 (minor), whereas the esters bearing a strong electron-withdrawing grou
## Abstract New and efficient one pot syntheses of 2‐thioureidobenzimidazole (__V__), 2‐thioureidobenzoxazole (__VI__), and 2‐thioureidobenzothiazole (__VII__) have been developed. The target compounds were obtained in good yields by condensing the title synthon commonly known as isoperthiocyanic a