Studies on Tertiary Amine Oxides. LXXX. Reaction of Quinoline 1-Oxide with Phenylacetic Anhydride

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Author(s)

Abstract

Treatment of quinoline 1-oxide (1) with phenylacetic acid and acetic anhydride in boiling benzene for 10 h gave benzaldehyde (2), quinoline (3), 2-benzylquinoline (4), 2-benzoylquinoline (5), phenyl-di (2-quinolyl) carbinol (6), di (2-quinolyl) ketone (7), and N-(2-quinolyl)-2-benzylidene-1,2-dihydroquinoline (8) in small yields. The reaction of 1 with phenylacetic anhydride in boiling benzene for 10 h afforded 1,3-diphenyl-1-(2-quinolyl) acetone (9) and dibenzyl ketone (10) together with small amounts of 2,3,and 5. Further, it was found that phenylacetic anhydride undergoes decarboxylative coupling upon heating with tertiary amines to give 10. The mechanisms of these reactions are discussed.

Journal

  • Chemical & pharmaceutical bulletin

    Chemical & pharmaceutical bulletin 32(10), 3886-3891, 1984-10-25

    The Pharmaceutical Society of Japan

Codes

  • NII Article ID (NAID)
    110003624650
  • NII NACSIS-CAT ID (NCID)
    AA00602100
  • Text Lang
    ENG
  • ISSN
    00092363
  • Data Source
    NII-ELS 
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