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Synthesis of 3-thiocyanato-1H,3H-quinoline-2,4-diones

✍ Scribed by Antonín Klásek; Jirí Polis; Vladimír Mrkvička; Janez Košmrlj

Publisher
Journal of Heterocyclic Chemistry
Year
2002
Tongue
English
Weight
49 KB
Volume
39
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

4‐Hydroxy‐1__H__‐quinolin‐2‐ones (1) react with thiocyanogen in acetic acid to the corresponding 3‐thiocyanato‐1__H__,3__H__‐quinoline‐2,4‐diones (2) in good yields. In some cases, 3‐bromo‐1__H__,3__H__‐quinoline‐2,4‐diones (4) were isolated as minor reaction products. Compounds 2 are very reactive towards nucleophiles and easily hydrolyze to the corresponding 4‐hydroxy‐1__H__‐quinoline‐2‐ones (1).

📜 SIMILAR VOLUMES

1-Methyl-3-phenyl-3-thiocyanato-1H,3H-qu
1-Methyl-3-phenyl-3-thiocyanato-1H,3H-quinoline-2,4-dione: A novel thiocyanating agent
✍ Antonín Klásek; Vladimír Mrkvička 📂 Article 📅 2003 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 57 KB

## Abstract Under mild reaction conditions, the thiocyanato group is selectively transferred from 1‐methyl‐3‐phenyl‐3‐thiocyanato‐1__H__,3__H__‐quinoline‐2,4‐dione (**3**) to some nucleophiles. Aliphatic primary and secondary amines are converted to S‐cyanothiohydroxylamines, anilines afford __p__‐