Photochemical, alkylation of nitrogen heteroaromatics by carboxylic acids under decarboxylation

✍ Scribed by H. Nozaki; M. Katô; R. Noyori; M. Kawanisi

• Publisher: Elsevier Science
• Year: 1967
• Tongue: French
• Weight: 108 KB
• Volume: 8
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)73009-7

✦ Synopsis

We wish to report that the title reaction as applied to a combination of quinoline and acetic acid proceeds under irradiation of the benzene solution with 200W high pres-(Received in Japan 17 Lh11y 1967) sure meroury 8rc and gives a mixture of 2-methyl-, J-methyl-and 2,44imethylquinolines.

Extention to other couples of benzopyridinee 8nd oarboxylic acids gave results as summ8rized in Table .

The mechanism of this novel type of alkylation should account for following observations made: A. Pyridine itzelf remained unchanged upon similar.treatment. B. The alkylation occurred formelly at the electron-deficient ground state (1). positions in the C. An increase of the carbon number of fattv acids gave better yields. D. No skeletal change was observed in the alkyl part of isovaleric 8cid. E. Attempted reaction of phenanthrene and acetic acid failed. The reaction of quinoline and ecetic acid in the presence of 0.2-0.5 mole ratio of phenanthrene gave no methylsted phenanthrene.