Interrupted Nazarov cyclization on silica gel.
Exposure of a mixture of propargyl vinyl ketone and a nucleophilic primary or secondary amine to activated dry silica gel in the absence of solvent leads to a cascade of reactions that results in the formation of an aminocyclopentenone. The reaction with triethylamine leads to a cross-conjugated cyclopentadienone.
Dhoro
Francis
F
Department of Chemistry, 2545 The Mall, University of Hawaii, Honolulu, Hawaii 96822, USA.
Tius
Marcus A
MA
D003500:Cyclization; D005782:Gels / Q000737:chemistry; D007202:Indicators and Reagents; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012822:Silicon Dioxide / Q000737:chemistry*
D005782:Gels; D007202:Indicators and Reagents; D007659:Ketones; D012822:Silicon Dioxide