Preparation and proton spectra of 1‐aryl‐1,2‐dihydro‐2‐quinolones | Zendy

Wawzonek Stanley | Zendy; Van Truong Thien | Zendy

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Preparation and proton spectra of 1‐aryl‐1,2‐dihydro‐2‐quinolones

Author(s) -

Wawzonek Stanley,

Van Truong Thien

Publication year - 1988

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.5570250205

Subject(s) - chemistry , aryl , isoquinoline , quinolone , bromide , mass spectrum , proton , medicinal chemistry , potassium bromide , derivative (finance) , potassium , stereochemistry , organic chemistry , ion , biochemistry , alkyl , physics , quantum mechanics , financial economics , economics , antibiotics

1‐Phenyl‐, 1‐ m ‐tolyl‐ and 1‐ p ‐tolyl‐1,2‐dihydro‐2‐quinolone have been prepared by treating the potassium derivative of 1,2‐dihydro‐2‐quinolone with the corresponding aryl bromide in the presence of finely divided copper. The use of o ‐bromotoluene in this reaction gave trace amounts of a crystalline material which upon the basis of mass spectrum analysis was assigned 2‐ o ‐tolyloxyquinoline as a structure. The 1‐aryl groups caused an unusual chemical shift of the 8‐proton to the Δ 6.64–6.70 region. This behavior paralleled that observed for the 7‐proton of 6‐phenyl‐6 H ‐indeno[1,2‐ c ]isoquinoline‐5,11‐dione in earlier studies.

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