The formation of the indolizino[1,2‐ c ]quinolinium system by a novel nucleophilic reaction | Zendy

Bradsher Charles K. | Zendy; Burnham Weldon S. | Zendy; Zinn Mary F. | Zendy

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The formation of the indolizino[1,2‐ c ]quinolinium system by a novel nucleophilic reaction

Author(s) -

Bradsher Charles K.,

Burnham Weldon S.,

Zinn Mary F.

Publication year - 1970

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.5570070405

Subject(s) - chemistry , ethyl bromoacetate , nucleophile , derivative (finance) , medicinal chemistry , quinoline , bromide , ketone , organic chemistry , catalysis , financial economics , economics

2‐Methyl‐3‐(2‐pyridyl)quinoline (1) with a bromomethyl ketone or ethyl bromoacetate yields 6‐methyl‐12‐acylindolizino[1,2‐ c ]quinolinium bromides ( 5–9 ). The acyl derivatives can be deacylated in acid yielding 6‐methyl indolizino[1,2‐ c ]quinolinium salts ( 4 ). Benzoylation of 4 yields the 12‐benzoyl derivative ( 6 ). The deacylation product ( 4 ) has been synthesized from 2‐acetamidophenacyl bromide ( 10 ) and 2‐pyridylacetone ( 12 ).

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