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Studien zur Chemie von thienoanellierten O,N‐ und S,N‐haltigen Heterocyclen, 8. Synthese eines racemischen, thienoanalogen Diltiazems mit potentieller Calciumkanal blockierender Wirkung
Author(s) -
Laimer Ingrid,
Erker Thomas
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199519950260
Subject(s) - chemistry , alkylation , stereochemistry , acetylation , medicinal chemistry , derivative (finance) , catalysis , organic chemistry , biochemistry , financial economics , economics , gene
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 .