A new synthesis of ‘push–pull’ naphthalenes by condensation of nitro-2-methylbenzoate esters with dimethylacetamide dimethyl acetal
✍ Scribed by See-Mun Wong; Bhavini Shah; Priyal Shah; Ian C. Butt; Esther C.Y. Woon; James A. Wright; Andrew S. Thompson; Christopher Upton; Michael D. Threadgill
- Book ID
- 104250652
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 102 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
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-3dimethylamino-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.