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A simple and convenient one-pot synthesis of substituted isoindolin-1-ones via lithiation, substitution and cyclization of N'-benzyl-N,N-dimethylureas

Author(s): Keith Smith | Gamal A. El-Hiti | Amany S. Hegazy | Benson Kariuki

Journal: Beilstein Journal of Organic Chemistry
ISSN 1860-5397

Volume: 7;
Issue: 1;
Start page: 1219;
Date: 2011;
Original page

Keywords: N'-benzyl-N | N-dimethylureas | isoindolin-1-ones | directed lithiation | electrophiles | substitution | synthesis

Lithiation of N'-benzyl-N,N-dimethylurea and its substituted derivatives with t-BuLi (3.3 equiv) in anhydrous THF at 0 °C followed by reaction with various electrophiles afforded a range of 3-substituted isoindolin-1-ones in high yields.

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