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The preparation of 3-substituted 1,2-benzisothiazole-1,1-dioxides from the condensation-cyclization of dilithiated β-ketoesters with methyl 2-(aminosulfonyl)benzoate or 1,2-benzisothiazol-3(2H)-one-1,1-dioxide

✍ Scribed by Michelle A. Meierhoefer; Matthew J. Walters; S. Patrick Dunn; Jarrett H. Vella; Bonnie J. Grant; Carolyn L. Sober; Nidhi S. Patel; Laela M. Hajiaghamohseni; Sara B. Lioi; Clyde R. Metz; Charles F. Beam; William T. Pennington; Donald G. Vanderveer; N. Dwight Camper

Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
144 KB
Volume
43
Category
Article
ISSN
0022-152X

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✦ Synopsis

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-sulfonamide, a single βketoester tautomer is usually formed after recrystallization from ethanol. The same dilithiated β-ketoesters generally condense less well with 1,2-benzisothiazol-3(2H)-one-1,1-dioxide (saccharin) under the same conditions to afford the same products usually in the same or lower yields. The use of N,N,N',N'-tetramethylethylenediamine during these syntheses has sometimes resulted in improved yields of products.

📜 SIMILAR VOLUMES

The Preparation of 3-Substituted 1,2-Ben
The Preparation of 3-Substituted 1,2-Benzisothiazole-1,1-dioxides from the Condensation—Cyclization of Dilithiated β-Ketoesters with Methyl 2-(Aminosulfonyl)benzoate or 1,2-Benzisothiazol-3(2H)-one-1,1-dioxide.
✍ Michelle A. Meierhoefer; et al. et al. 📂 Article 📅 2006 🏛 John Wiley and Sons ⚖ 17 KB 👁 2 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

The preparation of 3-substituted 1,2-ben
The preparation of 3-substituted 1,2-benzisothiazole 1,1-dioxides from lithiated intermediates or grignard reagents and methyl 2-(aminosulfonyl)benzoate
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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

The preparation of benzoisothiazolo[1,2-
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
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## 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 h