Photoinduced [4 + 4] cycloadditions of o-quinones with oxazoles |
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Authors: | Zhang Yan Wang Lei Zhang Min Fun Hoong-Kun Xu Jian-Hua |
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Affiliation: | Department of Chemistry, Nanjing University, Nanjing 210093, China. |
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Abstract: | [reaction: see text] Photocycloadditions of 9,10-phenanthraquinone (PQ) with oxazoles (1a and 1b) gave [4 + 4] products 2 with the O=C-C=O functionality in PQ and the 2-azadiene moiety in oxazole as 4pi addends. Photoreactions of 1-acetylisatin (IS) with 1a, 1c, and 1d gave [4 + 4] product A, which underwent further [2 + 2] reactions with another (3)IS to furnish 5. These regioselective and diastereoselective [4 + 4] photocycloadditions are rationalized by the intervening of the key conformers for ISC and bond formation of the most stable 1,6-diradical intermediates. |
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