2,6‐Diarylhexahydro‐4‐pyridazinols by acid‐catalyzed cyclization of benzaldehyde aryl‐2‐(2‐propenyl)hydrazones | Zendy

Bakthavatchalam Rajagopal | Zendy; Ciganek Engelbert | Zendy; Calabrese Joseph C. | Zendy

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2,6‐Diarylhexahydro‐4‐pyridazinols by acid‐catalyzed cyclization of benzaldehyde aryl‐2‐(2‐propenyl)hydrazones

Author(s) -

Bakthavatchalam Rajagopal,

Ciganek Engelbert,

Calabrese Joseph C.

Publication year - 1996

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.5570330137

Subject(s) - chemistry , propenyl , benzaldehyde , yield (engineering) , hydrazone , hydrazine (antidepressant) , sulfuric acid , organic chemistry , aryl , medicinal chemistry , catalysis , chromatography , materials science , alkyl , metallurgy

Treatment of benzaldehyde l‐(2‐propenyl)‐4‐methylsulfonylphenylhydrazone ( 1f ) with 45% sulfuric acid gave 2‐(4‐methylsulfonylphenyl)‐6‐phenylhexahydro‐4‐pyridazinol ( 2f ) in 35% yield rather than the expected 1‐(4‐methylsulfonylphenyl)‐1‐(2‐propenyl)hydrazine. The halogen‐substituted hydrazones 1c‐1e and benzaldehyde 1‐(2‐methyl‐2‐propenyl)phenylhydrazone ( 1b ) gave similar results.

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