Reaction of polyhaloalkyl-substituted chromones, pyrones, and furanones with salicylaldehydes as a direct route to fused 2H-chromenes.
Polyhaloalkyl-substituted chromones, gamma-pyrones, and beta-furanones react with salicylaldehydes in the presence of piperidine to give a wide variety of fused 2H-chromenes in good yields. This novel annulation reaction presumably proceeds by a tandem intermolecular oxa-Michael addition and subsequent intramolecular Mannich condensation.
Sosnovskikh
Vyacheslav Ya
VY
Department of Chemistry, Ural State University, 620083 Ekaterinburg, Russian Federation. vyacheslav.sosnovskikh@usu.ru
Korotaev
Vladislav Yu
VY
Chizhov
Dmitry L
DL
Kutyashev
Igor B
IB
Yachevskii
Danil S
DS
Kazheva
Olga N
ON
Dyachenko
Oleg A
OA
Charushin
Valery N
VN
D000447:Aldehydes / Q000737:chemistry; D001578:Benzopyrans / Q000138:chemical synthesis*; D002867:Chromones / Q000737:chemistry; D005663:Furans / Q000737:chemistry; D011753:Pyrones / Q000737:chemistry
D000447:Aldehydes; D001578:Benzopyrans; D002867:Chromones; D005663:Furans; D011753:Pyrones; C013243:salicylaldehyde