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- W1408954816 abstract "A variation of the Madelung cyclization involves installing a functional group at the o -methyl group, which can facilitate cyclization. For example, a triphenylphosphonio substituent converts the reaction into an intramolecular Wittig condensation. The required phosphonium salts can be prepared by starting with o -nitrobenzyl chloride or bromide. Retrosynthetic path has recently been realized as an effective synthesis of 2, 3-disubstituted indoles using low-valent titanium reagents to affect the reductive cyclization. Several aryl- and methyl-substituted compounds were prepared by using Ti-graphite prepared from K-graphite and TCl 3 . An improved methodology which avoids the preparation of K graphite was subsequently developed. This procedure uses zinc powder to effect in situ reduction of TiCl 3 . A stirred solution of o -methylpivalanilide (50 mmol) in dry THF (100 ml) was maintained at 15 O C under a nitrogen atmosphere. A 1.5 M solution of n-butyllithium in hexane (3 equiv.) was added dropwise. The solution was then maintained at room temperature for 16 h. The solution was cooled in an ice-bath and treated with 2 N HCI (60ml). The organic layer was separated and the aqueous layer was further extracted with benzene. The combined layers were dried (MgSO 4 ). The product was obtained in 87% yield and recrystallized from ether-cyclohexane." @default.
- W1408954816 created "2016-06-24" @default.
- W1408954816 creator A5032729431 @default.
- W1408954816 date "1996-01-01" @default.
- W1408954816 modified "2023-09-27" @default.
- W1408954816 title "Category Ia Cyclizations" @default.
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