TY - JOUR
T1 - Reactions of enaminones with diazocarbonyl compounds
AU - Güngör, Füsun Şeyma
AU - Hancioǧlu, Neslihan
AU - Anaç, Olcay
PY - 2013/3
Y1 - 2013/3
N2 - The [Cu(acac)2]-catalyzed reactions of several tertiary enaminones with three diazocarbonyl compounds, i.e., dimethyl diazomalonate, ethyl diazoacetoacetate, and ethyl diazoacetate, yielded amino- and additionally carbonyl-substituted dihydrofurans, together with further furan derivatives. Due to the conjugation of α-carbonyl/α-Ph groups, reactions proceeded only via 1,5-electrocyclization of corresponding keto-ylides. On the other hand, in the absence of any α-substituent, tertiary enaminone and ethyl diazoacetate, reacted via an accompanying mechanism by a push-pull cyclopropane intermediate, to yield a 2,4-dicarbonyl-substituted furan in one step with moderate yield.
AB - The [Cu(acac)2]-catalyzed reactions of several tertiary enaminones with three diazocarbonyl compounds, i.e., dimethyl diazomalonate, ethyl diazoacetoacetate, and ethyl diazoacetate, yielded amino- and additionally carbonyl-substituted dihydrofurans, together with further furan derivatives. Due to the conjugation of α-carbonyl/α-Ph groups, reactions proceeded only via 1,5-electrocyclization of corresponding keto-ylides. On the other hand, in the absence of any α-substituent, tertiary enaminone and ethyl diazoacetate, reacted via an accompanying mechanism by a push-pull cyclopropane intermediate, to yield a 2,4-dicarbonyl-substituted furan in one step with moderate yield.
KW - Carbenoids
KW - Diazo compounds
KW - Electrocyclic reactions
KW - Enaminones
KW - Furans, dihydro-
UR - http://www.scopus.com/inward/record.url?scp=84875273020&partnerID=8YFLogxK
U2 - 10.1002/hlca.201200233
DO - 10.1002/hlca.201200233
M3 - Article
AN - SCOPUS:84875273020
SN - 0018-019X
VL - 96
SP - 488
EP - 493
JO - Helvetica Chimica Acta
JF - Helvetica Chimica Acta
IS - 3
ER -