See-Mun Wong, Bhavini Shah, Priya V. Shah
Mar 18, 2002
Citations
2
Influential Citations
11
Citations
Journal
Tetrahedron Letters
Abstract
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.