期刊
ORGANIC LETTERS
卷 24, 期 16, 页码 3092-3096出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01135
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资金
- Universita degli Studi dell'Insubria
- Universita degli Stud i di Milano
Treatment of aldehyde-substituted isoxazol-5(4H)-ones with [RuCl2(p-cymene)](2) as the catalyst generates pyrazole-4-carboxylic acids, while treatment of alcohol-substituted isoxazol-5(4H)-ones produces isoxazole-4-carboxylic acids. The presence of intramolecular hydrogen bonding in the substrates plays a crucial role in diverting the reaction towards ring-opening non-decarboxylative pathway.
Treatment of 4-(2-hydroaminoalkylidenyl)- and 4-(2-hydroxyalkylidenyl)-substituted isoxazol-5(4H)-ones with catalytic amounts of [RuCl2(p-cymene)](2), without any additive, afforded pyrazole- and isoxazole-4-carboxylic acids, respectively. The presence of an intramolecular H-bond in these substrates was the key to divert the classical mechanism toward a ring-opening non-decarboxylative path that is expected to generate a vinyl Ru-nitrenoid intermediate, the cyclization of which affords the rearranged products. A gram scale protocol demonstrated the synthetic applicability of this transformation.
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