Tetrahedron letters

A new synthesis of 'push–pull'naphthalenes by condensation of nitro-2-methylbenzoate esters with dimethylacetamide dimethyl acetal

…, P Shah, IC Butt, ECY Woon, JA Wright, AS Thompson…

文献索引：Wong, See-Mun; Shah, Bhavini; Shah, Priyal; Butt, Ian C.; Woon, Esther C.Y.; Wright, James A.; Thompson, Andrew S.; Upton, Christopher; Threadgill, Michael D. Tetrahedron Letters, 2002 , vol. 43, # 12 p. 2299 - 2302

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被引用次数: 13

摘要

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 ...