Base‐catalyzed cyclization reactions of 2‐[2‐(2,4‐dimethyl‐3‐oxopentyl)]benzimidazoles with acetic anhydride and its homologs | Zendy

Linke Siegfried | Zendy; Wünsche Christian | Zendy

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Base‐catalyzed cyclization reactions of 2‐[2‐(2,4‐dimethyl‐3‐oxopentyl)]benzimidazoles with acetic anhydride and its homologs

Author(s) -

Linke Siegfried,

Wünsche Christian

Publication year - 1973

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.5570100310

Subject(s) - acetic anhydride , chemistry , yield (engineering) , steric effects , base (topology) , catalysis , medicinal chemistry , organic chemistry , mathematical analysis , materials science , mathematics , metallurgy

2‐[2‐(2,4‐Dimethyl‐3‐oxopentyl)]benz, imidazoles ( 2‐10 ) were obtained by allowing o ‐phenyl‐enediamines to react with 2,2,4,4‐tetramethyl‐1,3‐cyclobutanedione ( 1 ). When refluxed with acetic anhydride (or sterically unhindered homologs) they cyclize in the presence of base to yield the pyrido[1,2‐α]benzimidazoles ( 16‐21 and 24, 25 ). The 2‐[2‐(2,4‐dimethyl‐3‐oxo‐pentyl) ]imidazolines ( 12 and 14 ) were obtained by reaction of 1,2‐diaminoethane and 1,2‐diaminopropane, respectively, with 1 . When allowed to react with acetic anhydride/base, they gave only N ‐acylated products.

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