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Preparation of spiro[benzoisothiazole-isoxazole] dioxides from dilithiated c(α),O-oximes and methyl 2-(aminosulfonyl)benzoate

✍ Scribed by Bonnie J. Grant; Catherine R. Kramp; John D. Knight; Michelle A. Meierhoefer; Jarrett H. Vella; Carolyn L. Sober; Stephen S. Jones; Clyde R. Metz; Charles F. Beam; William T. Pennington; Donald G. Vanderveer; N. Dwight Camper


Publisher
Journal of Heterocyclic Chemistry
Year
2007
Tongue
English
Weight
436 KB
Volume
44
Category
Article
ISSN
0022-152X

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✦ Synopsis


Abstract

magnified image

Several dilithiated C(α), O‐oximes were prepared in excess lithium diisopropylamide‐tetramethyl‐ethylenediamine (LDA/TMEDA) and condensed with methyl 2‐(aminosulfonyl)benzoate followed by acid cyclization of intermediates to spiro(benzoisothiazole‐isoxazole) dioxides, a new spiro and fused‐ring system. Distortionless enhancement by polarization transfer (DEPT) and liquid chromatography mass spectrometry (LCMS) for all products, as well as X‐ray single crystal analysis on a representative product, were especially relevant for structure confirmation in this synthesis.


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