Substituierte 4-Amino-thieno[2,3-c]isothiazole und 4-Amino-thieno[3,2-d]isothiazole

✍ Scribed by Doz. Dr. K. Gewald; Dipl. Chem. W. Radke; U. Hain

• Book ID: 105352238
• Publisher: John Wiley and Sons
• Year: 1980
• Tongue: English
• Weight: 586 KB
• Volume: 322
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/prac.19803220620

✦ Synopsis

Substituted 4‐Amino‐thieno[2,3‐c]isothiazoles and 4‐Amino‐thieno[3,2‐d]isothiazoles

The alkylation of disodium‐(4‐cyanisothiazole‐3,5)‐dithiolate 1 with α‐chloro carbonyl compounds followed by THORPE‐ZIEGLER‐cyclization yields the substituted 4‐amino‐thieno[3,2‐d]isothiazoles 3, which can be converted into the thieno‐isothiazolo‐1,4‐thiazepine derivatives 4, 5. The successive alkylation of 1 with dimethylsulfate and α‐chloro carbonyl compounds yields the 5‐methylthio‐isothiazole‐4‐carbonitriles 11 which are cyclized to form the substituted 4‐amino‐3‐methylthio‐thieno[3,2‐d]isothiazoles 13. The inverse alkylation procedure leads to the isomeric 4‐amino‐3‐methylthio‐thieno[2,3‐c]isothiazoles 20. Successive alkylation of the 3‐hydroxy‐5‐mercapto‐4‐cyanoisothiazoles 14 with α‐chloro carbonyl compounds and diazomethane followed by cyclization yields the 4‐amino‐3‐methoxy‐thieno[3,2‐d]isothiazoles 17. From 13 and 20 the isothiazole‐thieno‐pyrimidines 21, 22 and the isothiazolo‐thieno‐oxazinone 25 are synthesized.