Synthesis of some new indolizines | Zendy

Sarkunam K. | Zendy; Nallu M. | Zendy

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Synthesis of some new indolizines

Author(s) -

Sarkunam K.,

Nallu M.

Publication year - 2005

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.5570420102

Subject(s) - indolizine , chemistry , pyridinium , ylide , yield (engineering) , bromide , aqueous solution , medicinal chemistry , organic chemistry , materials science , metallurgy

The reaction between 4‐dimethylaminopyridine (DMAP) and 2‐bromoacetophenone(s) readily gives 1‐ [2‐(4‐substitutedphenyl)‐2‐oxoethyl]‐4‐(dimethylamino)pyridinium bromide ( 1–14 ). Action of aqueous NaOH on 1–8 generates the corresponding pyridinium ylide ( 15–22 ), which is isolated as a colored stable crystalline solid. Addition of 15–22 to dimethylacetylene dicarboxylate (DMAD) gives dimethyl 3‐(substitutedbenzoyl)‐7‐(dimethylamino)indolizine‐1,2‐dicarboxylate ( 23–30 ) in 46–62% yield.

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