Synthesis and Structure of Geminally Activated Nitroethenes of the Indole Series

Primary nitro compounds: progress in the synthesis of isoxazoles by condensation with aldehydes or activated ketones

“…Other nitroenones 18 are reported under different experimental conditions: Al 2 O 3 in CH 2 Cl 2 at room temperature, 57 thionyl chloride in ethanol at rt or heating 58,59 and β-alanine and acetic acid in benzene under reflux; 60–65 phosphoryl chloride in ethanol at room temperature; 66 acetic anhydride at 120–130 °C, 67 (2 S )-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine and 4-nitro-benzoic acid in dichloromethane; 68 and 4-methyl-morpholine and titanium tetrachloride at 0 °C. 69…”

Nitroacetonitrile and Its Synthetic Equivalents

“…Thus, NAN serves as a nucleophile leading to alkenes 8 substituted with cyano and nitro groups (Scheme ). This protocol is useful for generating a library of compounds by simply altering aldehydes 7 , which facilitates biological activity evaluation. − The synthesis of push–pull alkenes (Ar = electron rich aryl), applicable in the development of nonlinear optical materials, is readily achieved upon treatment of NAN with electron-rich aldehydes. , When α,β-unsaturated aldehydes 9 (Ar = substituted phenyl, heteroaryl) are used, nucleophilic attack of NAN (1,2-addition) occurs at the formyl group to afford butadienes 10 in moderate yields (Scheme ). , Thioamides are also applicable as substrates in place of aldehydes 7 for condensation with NAN .…”