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Reactions of Enaminones with Diazocarbonyl Compounds
Author(s) -
Şeyma Güngör Füsun,
Hancıoğlu Neslihan,
Anaç Olcay
Publication year - 2013
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200233
Subject(s) - chemistry , ethyl diazoacetate , furan , cyclopropane , substituent , yield (engineering) , medicinal chemistry , catalysis , organic chemistry , cyclopropanation , ring (chemistry) , materials science , metallurgy
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.