Synthesis of 8,9‐dialkoxybenzodiazepines and 7,8‐dialkoxyisoquinolines | Zendy

Pongó Lészló | Zendy; Reiter Józef | Zendy; Simig Gyula | Zendy; ágai Béla | Zendy; Faigl Ferenc | Zendy

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Synthesis of 8,9‐dialkoxybenzodiazepines and 7,8‐dialkoxyisoquinolines

Author(s) -

Pongó Lészló,

Reiter Józef,

Simig Gyula,

ágai Béla,

Faigl Ferenc

Publication year - 2006

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.5570430617

Subject(s) - chemistry , hydrazine (antidepressant) , hydroxylamine hydrochloride , hydrochloride , acylation , ammonia , hydroxylamine , diketone , organic chemistry , medicinal chemistry , catalysis , chromatography

o ‐Aroylarylacetone type 1,5‐diketone derivatives (5, 6) were synthesised from arylacetones (1) protected as 1,3‐dioxolanes (4) through directed ortho lithiation followed by acylation with aroyl chlorides. 8,9‐Dialkoxy‐2,3‐benzodiazepines 9 were obtained by cyclisation of diketones 6 with hydrazine. The reaction of diketones 6 with ammonia gave 7,8‐dialkoxyisoquinolines 11. Reaction of ketals 5 with hydrazine hydrochloride and hydroxylamine hydrochloride afforded N ‐amino‐7,8‐dialkoxyisoquinolinium chlorides (10) and 7,8‐dialkoxyisoquinolinium oxides (12), respectively.

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