Reaction of 2-propargylphenylcarbamates with diphenyliodonium salts via Meyer-Schuster rearrangement. Issue 45 (8th November 2017)

• Record Type: Journal Article
• Authors: Minami, Hideki; Okamoto, Noriko; Sueda, Takuya; Sakaguchi, Takatsugu; Ishikura, Minoru; Yanada, Reiko
• Is Part Of: Tetrahedron letters. Volume 58:Issue 45(2017)
• Page Start: 4277
• Page End: 4280
• Publication Date: 2017-11-08
• Subjects: Quinolone -- Meyer-Schuster rearrangement -- Michael addition -- Indenone -- Friedel-Crafts alkylation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.09.079
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: The syntheses of dihydroquinolones from 2-propargylphenylcarbamates were achieved. The syntheses of arylated dihydroquinolones by two steps were achieved. The syntheses of arylated dihydroquinolones by one-pot reaction were achieved. The syntheses of dihydroindenones by one-pot reaction were achieved. Abstract: The syntheses of 2, 3-dihydro-4-quinolones from 2-propargylphenylcarbamates by one-pot tandem process that involves Meyer-Schuster rearrangement or arylative Meyer-Schuster rearrangement/Michael addition of carbamate nitrogen to the resulting vinyl ketones have been developed. Phenylcarbamates tethering tertiary propargyl alcohols underwent arylative Meyer-Schuster rearrangement/Friedel-Crafts alkylation to produce 2, 3-dihydroindenones.