A new route to 2-substituted perimidines based on nitrile oxide chemistry
β Scribed by Iain A.S. Smellie; Andreas Fromm; R. Michael Paton
- Publisher
- Elsevier Science
- Year
- 2009
- Tongue
- French
- Weight
- 245 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
A new route to perimidines has been developed which involves reaction of a nitrile oxide with 1,8-diaminonaphthalene. Benzonitrile oxide, generated by dehydrochlorination of benzohydroximoyl chloride, and 1,8-diaminonaphthalene afforded 2-phenylperimidine. 2-Pyranosylperimidines were prepared by the same approach from pyranosyl hydroximoyl chlorides.
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## Abstract 4,9βDimethoxynaphtho[2,3β__b__]furan 9 was obtained in 91% yield __via__ the reductive methylation of naphtho[2,3β__b__]furanβ4,9βdione 2. After treatment of 9 with butyllithium, the mixture was allowed to react with __N,N__βdimethylacetamide, followed by oxidization with cerium(IV) dia