SYNTHESIS OF NOVEL 5,6,7,8-TETRAHYDRO-4H-THIENO[2,3-B][1,4]-DIAZEPINEDERIVATIVES

Citation
H. Cho et al., SYNTHESIS OF NOVEL 5,6,7,8-TETRAHYDRO-4H-THIENO[2,3-B][1,4]-DIAZEPINEDERIVATIVES, Heterocycles, 48(8), 1998, pp. 1555-1566
Citations number
5
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
0385-5414
Volume
48
Issue
8
Year of publication
1998
Pages
1555 - 1566
Database
ISI
SICI code
0385-5414(1998)48:8<1555:SON5>2.0.ZU;2-W
Abstract
Unsubstituted 5,6,7, 8-tetrahydro-4H-thieno[2, 3-b][1,4]diazepine (1) and 4H-thieno[2,3-b][1,4]diazepine-5,7(6H,8H)-dione (2) were newly syn thesized. Benzoylation of 1 regioselectively afforded thienodiazepine (13) substituted with a benzoyl group nl position 4. Alternatively, no vel synthetic procedures were devised to yield thienodiazepine (22) su bstituted with an alkyl group or compound (14) with an aralkyl group a t position 8. Thus, the ingenious introduction of functional groups at the N-4 or 8 position of a thienodiazepine skeleton was achieved and then a variety of 5,6,7,8-tetrahydro-4H-thieno[2,3-b][1,4]diazepines ( 5)-(9), and (27), some of which exhibited potent arginine vasopressin antagonistic activity, were obtained using the key intermediates and ( 1), (13), (14) and (22).