Abstract
The AuCl-catalyzed benzannulation of ortho-alkynylphenyl ketones with benzenediazonium 2-carboxylate proceeded efficiently at 40 °C in (CH2Cl)2 and a variety of anthracene derivatives, having a ketone group at 9-position, were produced in good to high yields. On the other hand, the reaction of ortho-alkynylbenzaldehydes with benzenediazonium 2-carboxylate afforded triptycyl ketones. The reactions most probably proceed through the formation of a zwitterionic intermediate by the gold-induced electrophilic cyclization of ortho-alkynyl(oxo)benzenes, followed by the cycloaddition of benzyne. In contrast, when the above reaction was carried out at rt in 1,4-dioxane, phthalazine derivative was produced without the generation of benzyne.
Original language | English |
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Pages (from-to) | 787-796 |
Number of pages | 10 |
Journal | Tetrahedron |
Volume | 64 |
Issue number | 5 |
DOIs | |
Publication status | Published - 2008 Jan 28 |
Keywords
- Anthracene
- Benzannulation
- Benzyne
- Gold catalyst
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry