Author/Authors :
Wong، نويسنده , , See-Mun and Shah، نويسنده , , Bhavini and Shah، نويسنده , , Priyal and Butt، نويسنده , , Ian C. and Woon، نويسنده , , Esther C.Y. and Wright، نويسنده , , James A. and Thompson، نويسنده , , Andrew S. and Upton، نويسنده , , Christopher and Threadgill، نويسنده , , Michael D.، نويسنده ,
Abstract :
Whereas condensation of 2-methyl-3-nitrobenzoate esters with dimethylformamide dimethyl acetal gives 5-nitroisocoumarin, analogous condensation with dimethylacetamide dimethyl acetal proceeds via a different route, affording 1-methoxy-3-dimethylamino-5-nitronaphthalene in good yield. Extension of the reaction to other naphthalenes with this novel ‘push–pull’ substitution motif has been explored. A deuterium labelling study revealed that equilibration of the alkoxy groups in the reaction mixture took place before the final carbocyclisation.
