Studien zur Chemie von thienoanellierten O,N- und S,N-haltigen Heterocyclen, 8. Synthese eines racemischen, thienoanalogen Diltiazems mit potentieller Calciumkanal blockierender Wirkung

✍ Scribed by Laimer, Ingrid ;Erker, Thomas

• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: English
• Weight: 414 KB
• Volume: 1995
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199519950260

✦ Synopsis

Studies on the Chemistry of Thieno‐Annulated O,N‐ and S,N‐Containing Heterocycles, 8^[1].^–Synthesis of a Racemic, Thieno Analogue Diltiazem with Potential Ca^2+^Antagonistic Activity

The synthesis of the thieno analogue diltiazem cis‐8‐[2‐(di‐methylamino)ethyl]‐5,6,7,8‐tetrahydro‐5‐(4‐methoxyphenyl)‐7‐oxothieno[3,2‐b][1,4]thiazepin‐6‐yl acetate (1) is described. Reaction of 3‐bromo‐2‐nitrothiophene with Na~2~S · 9H~2~O yields the intermediate 3‐mercapto‐2‐nitrothiophene (6), which reacts with the racemic glycidate 7 to give the racemic threo compound 10. Reduction and cyclization of 10 furnish the thieno [3,2‐b][1,4]thiazepine derivative 12. N‐Alkylation and acetylation of the hydroxy group of 12 leads to 1.