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).