Condensed heteroaromatic ring systems. XIX. Synthesis and reactions of 5-(tributylstannyl)isoxazoles

Takao Sakamoto, Yoshinori Kondo, Daishi Uchiyama, Hiroshi Yamanaka

Research output: Contribution to journalArticlepeer-review

44 Citations (Scopus)

Abstract

3-Substituted 5-(tributylstannyl)isoxazoles were newly synthesized by the 1,3-dipolar cyctoadditton of nitrile oxides to tributylethynylstannane. The iodination and the palladium-catalyzed benzoylation of 5-(tributylstannyl)-3-methylisoxazolegave 5-iodo-3-methylisoxazole and 3-methyl-5-isoxazolyl phenyl ketone in satisfactory yields, respectively. The palladium-catalyzed cross-coupling reaction of the stannylisoxazole with 2-bromonitrobenzene followed by the catalytic hydrogenation over Raney nickel resulted in the formation of 2-methyll-4(1H)-quinolinone in 57% overall yield.

Original languageEnglish
Pages (from-to)5111-5118
Number of pages8
JournalTetrahedron
Volume47
Issue number28
DOIs
Publication statusPublished - 1991

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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