- The behavior of 2-substituted-3-hydroxyisoindolinones in the reaction with sec-butyllithium
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This paper presents a dualistic behavior of 2-substituted-3- hydroxyisoindolones in reactions with sec-butyllithium (sec-BuLi). 2-tert-Butyl-3-hydroxy-2,3-dihydro-1H-isoindol-1-one (1a) treated with sec-BuLi undergoes metalation at position 7. On the other hand, the reaction between 3-hydroxy-2-phenyl-2,3-dihydroxyisoindol-1-one (1j) and sec-BuLi results in 3-sec-butyl-2-phenyl-2,3-dihydroisiondol-1-one (3j).
- Jozwiak,Ciechanska
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p. 357 - 362
(2014/04/17)
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- A BF3-mediated nitrogen-to-carbon rearrangement of N-protected 2,3-dihydro-3-hydroxy-1h-benzisoindol-1-ones, and its interception for a facile preparation of 3-substituted benzisoindolones
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A BF3-mediated release of the hydroxy and the nitrogen-protecting group of N-(cumyl or 1,1-diphenylethyl)-2,3-dihydro-3- hydroxy-1H-benzisoindol-1-ones is accompanied by recombination of the nitrogen-protecting unit to the 3-position of the rin
- Schwan, Adrian L.,Duspara, Petar A.,Paquette, Michelle M.,Merrill, A. Rod
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p. 3115 - 3119
(2008/02/13)
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- N-cumyl benzamide, sulfonamide, and aryl O-carbamate directed metalation groups. Mild hydrolytic lability for facile manipulation of directed ortho metalation derived aromatics
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(Matrix Presented) N-Cumyl benzamide (2), sulfonamide (8), and O-carbamate (11) compounds undergo directed ortho metalation under standard conditions to give, after quench with a variety of electrophiles, the substituted products 3, 9, and 12, respectively. Regiospecific and convenient approaches to phthalimides (7), 1,2-benzisothiazole 1,1-dioxides (10b), and ortho-substituted phenols (13a) and salicylamides (13b) are thereby established The mild deprotection protocol for these new cumyl directed metalation groups (DMGs) suggests that they will supersede previous corresponding groups for synthetic anionic aromatic chemistry.
- Metallinos, Costa,Nerdinger, Sven,Snieckus, Victor
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p. 1183 - 1186
(2008/02/09)
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