4 research outputs found
Three-Component Condensation of β-Ketonitriles, 4-Fluorobenzaldehyde, and Secondary Cyclic Amines
A new three-component condensation of β-ketonitriles, 4-fluorobenzaldehyde, and secondary cyclic amines was developed. A possible reaction mechanism has been proposed including Knoevenagel condensation followed by aromatic nucleophilic substitution. It was found that in the case of 3-oxopropanenitrile bearing the 6-amino-1,3-dimethyluracil moiety, the reaction is not accompanied by fluorine substitution in the Knoevenagel adduct, and the Michael addition of a secondary amine occurs followed by oxidation
Three-Component Condensation of β-Ketonitriles, 4-Fluorobenzaldehyde, and Secondary Cyclic Amines
A new three-component condensation of β-ketonitriles, 4-fluorobenzaldehyde, and secondary cyclic amines was developed. A possible reaction mechanism has been proposed including Knoevenagel condensation followed by aromatic nucleophilic substitution. It was found that in the case of 3-oxopropanenitrile bearing the 6-amino-1,3-dimethyluracil moiety, the reaction is not accompanied by fluorine substitution in the Knoevenagel adduct, and the Michael addition of a secondary amine occurs followed by oxidation
Divergent Transformations of 2‑Nitro‑1<i>H</i>‑benzo[<i>f</i>]chromenes in Reactions with Alkylidenemalononitriles: Access to Naphtho[2,1‑<i>b</i>]furans via Base-Mediated Pyran Ring Contraction
The action of 2-(1-arylethylidene)malononitriles
on 2-nitro-1H-benzo[f]chromenes
in the presence of
Et3N and MoO3·2H2O results in
naphtho[2,1-b]furans containing an allylidenemalononitrile
unit in the α-position. The reaction proceeds with contraction
of the pyran ring via a cascade carba-Michael addition/retro-oxa-Michael
reaction/tautomerization/SN2/oxidation process. In contrast,
the reaction of 2-nitro-1H-benzo[f]chromenes with the cyclic Knoevenagel adduct derived from 1-indanone
and malononitrile leads to dihydroindeno[1,2-c]xanthenes.
The possibility of further transformations of naphtho[2,1-b]furan derivatives as useful precursors and their optical
properties were also investigated