A general approach to the synthesis of substituted isoxazolo[4,3-c]quinolines via chalcones

作者：Madapa Sudharshan^*; Sridhar Divya; Yadav Gaya P; Maulik Prakas R; Batra Sanjay

来源：European Journal of Organic Chemistry, 2007, (26): 4343-4351.

• isoxazolo[4,3-c]quinolines
• 3-benzoylquinolin-4-ylamines
• reduction
• heterocyclization

A general and practical approach to the synthesis of substituted isoxazolo[4,3-c]quinolines from the substituted isoxazolines obtained by 1,3-dipolar cycloadditions between 2-nitrobenzonitrile oxide and chalcones is described. SnCl2-2H(2)O-mediated reduction of the nitro group, followed by intramolecular cyclization involving the amino and the keto groups in these substrates, furnished mixtures of isoxazolo[4,3-c]quinolines and 3,5-dihydroisoxazolo[4,3-c]quinolines. In contrast, the reduction of these substrates with Fe/AcOH unexpectedly yielded 3-benzoylquinolin-4-yl-amine derivatives.

• 出版日期2007-9