Synthesis of novel 5,6,7,8-tetrahydro-4H-thieno[2,3-b][1,4]-diazepine derivatives

Hidetsura Cho, Kengo Murakami, Akitaka Fujisawa, Misako Niwa, Hiroyuki Nakanishi, Itsuo Uchida

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

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 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).

Original languageEnglish
Pages (from-to)1555-1566
Number of pages12
JournalHeterocycles
Volume48
Issue number8
DOIs
Publication statusPublished - 1998 Jan 1

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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