MULTICOMPONENT DOMINO SYNTHESIS OF 2-(<i>tert</i>-BUTYL)-4<i>H</i>-PYRAN-3-CARBONITRILES AND THEIR PHOTOPHYSICAL PROPERTIES

Abstract

A concise and efficient one-pot synthetic method toward functionalized pyrans has been developed. Multicomponent domino reaction proceeds by mixing aromatic aldehyde, pivaloylacetonitrile, and (E)-N-methyl-1-(methylthio)-2-nitroethen-1-amine in the presence of NH4OAc under microwave irradiation in ethanol. This method was used to synthesize 13 new compounds. The structures of the compounds were confirmed by 1H and 13C NMR, IR, and ESI-MS. The results of their photophysical properties tests show that these compounds have good fluorescence intensity with excitation at 300 nm  wavelength. They displayed good solubility and large Stokes shifts (mostly more than 120 nm) in methanol. DFT and TDDFT calculations of the optical properties have been made.