The preparation of benzoisothiazolo[1,2-b][1,2]isoquinolin-11-one-1,1-dioxides from dilithiated ortho-toluic acids and lithiated methyl 2-(aminosulfonyl)benzoate
✍ Scribed by S. Patrick Dunn; Matthew J. Walters; Clyde R. Metz; Charles F. Beam; William T. Pennington; Mariusz Krawiec
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 2004
- Tongue
- English
- Weight
- 68 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
Select dilithiated ortho‐toluic acids were prepared in excess lithium diisopropylamide and condensed with methyl 2‐(aminosulfonyl)benzoate followed by a twofold cyclization of intermediates to afford benzoisothiazolo[1,2‐b][1,2]isoquinolin‐11‐one‐1,1‐dioxides, a new fused‐ring heterocyclic system.
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## Abstract A polylithiated β‐ketoester, β‐diketone, or β‐ketoamide was condensed‐cyclized with lithiated methyl 2‐(aminosulfonyl)benzoate, to afford new 3‐substituted 1,2‐benzisothiazole 1,1‐dioxides. Some Grignard or organolithium reagents were also condensed‐cyclized with methyl 2‐(aminosulfonyl
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Several β-ketoesters were dilithiated with an excess of lithium diisopropylamide, followed by condensation with methyl 2-(aminosulfonyl)benzoate to give intermediates that were not isolated but cyclized to 3substituted 1,2-benzisothiazole-1,1-dioxides. In most instances involving the ester-sulfonami
## Abstract magnified image A variety of substituted spiro(benzoisothiazole‐pyrazoles) have been prepared by the condensation of dilithiated __C__(α),__N__‐carboalkoxyhydrazones with lithiated methyl 2‐(aminosulfonyl)benzoate followed by the cyclization of intermediates with acetic anhydride, whic