Diazepines. III. Synthesis of 4 H ‐Pyrrolo[1,2‐ a ] thieno[3,2‐ f ] [1,4] diazepines | Zendy

Fujimori Hitoxhi | Zendy; Kayama Yasutaka | Zendy; Hara Takeshi | Zendy; Itoh Kazuhiko | Zendy; Sunami Tamiko | Zendy

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Diazepines. III. Synthesis of 4 H ‐Pyrrolo[1,2‐ a ] thieno[3,2‐ f ] [1,4] diazepines

Author(s) -

Fujimori Hitoxhi,

Kayama Yasutaka,

Hara Takeshi,

Itoh Kazuhiko,

Sunami Tamiko

Publication year - 1977

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570140214

Subject(s) - chemistry , hydrazine (antidepressant) , raney nickel , hydrate , acetic acid , ring (chemistry) , medicinal chemistry , bromine , methanol , diazepine , hydrolysis , condensation , organic chemistry , catalysis , physics , chromatography , thermodynamics

The synthesis of 4 H ‐pyrrolo[1,2‐ a ]thieno[3,2‐ f ] [1,4]diazepines ( 8 ) is described. Phthal‐imidomethylfurans 1 were treated with bromine‐methanol to give the dihydrofurans 2 , which were hydrolyzed and then liydrogenated over Raney nickel or with zinc‐acetic acid to afford the 1,4‐diketones 5 . Condensation of 2‐amino‐3‐benzoylthiophenes 6 with 5 gave 3‐benzoyl‐2‐pyrrolylthiopenes 7 . The removal of the phthaloyl group from 7 with hydrazine hydrate and ring closure to the diazepine ring yielded the new heterocycles 8 .

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