The use of α‐(aryl)‐4‐morpholineacetonitriles (masked acyl anion equivalents) in 1,4‐additions to α,β‐unsaturated esters and nitriles. A versatile synthetic route to 6‐aryl‐3(2H) pyridazinones

Abstract

The use of α‐(substituted‐phenyl)‐4‐morpholineacetonitriles in 1,4‐additions to ethyl acrylate, ethyl crotonate, methyl α‐methylacrylate, acrylonitrile, methylacrylonitrile, crotononitrile and cinnamonitrile was studied. A convenient route to 6‐aryl‐4,5‐dihydro‐3(2H) pyridazinones from aryl aldehydes and heterocyclic aldehydes was developed.

A Polyketone Synthesis Involving Nucleophilic Substitution via Carbanions Derived from Bis(α-aminonitrile)s. 5. A New, Well-Controlled Route to “Long” Bisphenol and Activated Aromatic Dihalide Monomers

“…Difluoro Monomer Containing Triphenylphosphine Oxide Moiety (12). Compound 11 was synthesized from aminonitrile 8 , and activated difluoride compound 10 − under the same conditions in 100% yield. Hydrolysis of compound 11 in 70% aqueous HOAc solution yielded the corresponding difluoro monomer 12 in 98% isolated yield.…”

Structural Optimization of 6-aryl Pyridazin­3-ones as Novel Potent PDE4 Inhibitors

“…Classical Friedel-Crafts reaction 14 using veratrol in presence of succinic anhydride and AlCl 3 afforded the dimethoxyphenyl derivative 7. The Strecker reaction 15 starting from the correctly substituted benzaldehyde 9 was also used for building the meta alkoxy derivative 11 (Scheme 1). The final compounds have been purified by flash chromatography.…”

Synthesis of 4‐aroyl‐5‐nitro‐1H‐imidazoles and 4‐aroyl‐5‐aminoimidazoles

“…Chemical shifts (6) are in ppm relative to internal tetramethylsilane. Samples for analysis were dried in uacuo over Drieritem at 70' for 16-25 hours.…”