TY - JOUR
T1 - Synthesis of novel 5,6,7,8-tetrahydro-4H-thieno[2,3-b][1,4]-diazepine derivatives
AU - Cho, Hidetsura
AU - Murakami, Kengo
AU - Fujisawa, Akitaka
AU - Niwa, Misako
AU - Nakanishi, Hiroyuki
AU - Uchida, Itsuo
PY - 1998/1/1
Y1 - 1998/1/1
N2 - 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 synthesized. Benzoylation of 1 regioselectively afforded thienodiazepine (13) substituted with a benzoyl group at position 4. Alternatively, novel synthetic procedures were devised to yield thienodiazepine (22) substituted with an alkyl group or compound (14) with an aralkyl group at 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 (1), (13), (14), and (22).
AB - 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 synthesized. Benzoylation of 1 regioselectively afforded thienodiazepine (13) substituted with a benzoyl group at position 4. Alternatively, novel synthetic procedures were devised to yield thienodiazepine (22) substituted with an alkyl group or compound (14) with an aralkyl group at 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 (1), (13), (14), and (22).
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U2 - 10.3987/COM-98-8179
DO - 10.3987/COM-98-8179
M3 - Article
AN - SCOPUS:0345207241
VL - 48
SP - 1555
EP - 1566
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
IS - 8
ER -