Synthesis of 1,4,5,6‐tetrahydropyrazolo[3,4‐ d ]pyrido[3,2‐ b ]azepine | Zendy

Albright J. Donald | Zendy; Du Xuemei | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

Synthesis of 1,4,5,6‐tetrahydropyrazolo[3,4‐ d ]pyrido[3,2‐ b ]azepine

Author(s) -

Albright J. Donald,

Du Xuemei

Publication year - 2000

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.5570370107

Subject(s) - azepine , chemistry , yield (engineering) , acrolein , acetic acid , stereochemistry , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy

The synthesis of 7,8‐dihydro‐5(6 H )‐quinolinone ( 3 ) from commercially available 3‐amino‐2‐cyclohexen‐1‐one ( 1 ) and 3‐(dimethylamino)acrolein ( 4 ) in 23% yield avoids the preparation of propynal ( 2 ). Conversion of 5‐(4‐methylphenylsulfonyl)‐6,7,8,9‐tetrahydro‐5 H ‐pyrido[3,2‐ b ]azepine ( 12 ) to 6‐(4‐methylphenylsulfonyl)‐1,4,5,6‐tetrahydropyrazolo[3,4‐ d ]pyrido[3,2‐ b ]azepine ( 24 ) is described. Removal of the N ‐(4‐methylphenylsulfonyl) group with 40% sulfuric acid in acetic acid gave the tricyclic azepine 26. Application of a similar series of reactions to 5‐(4‐nitrobenzoyl)‐6,7,8,9‐tetrahydro‐5 H ‐pyrido[3,2‐ b ]‐azepine ( 13 ) afforded 6‐(4‐nitrobenzoyl)‐1,4,5,6‐tetrahydropyrazolo[3,4‐ d ]pyrido[3,2‐ b ]azepine ( 25 ).

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research