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1,2,6-Thiadiazine 1-Oxides: Unsaturated Three-Dimensional S,N-Heterocycles from Sulfonimidamides

Jan-Hendrik Sch÷bel, Marco Thomas Passia, Nadja Anna Wolter, Rakesh Puttreddy, Kari Rissanen and Carsten Bolm*

*Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52074 Aachen, Germany, Email: carsten.bolmoc.rwth-aachen.de

J.-H. Sch÷bel, M. T. Passia, N. A. Wolter, R. Puttreddy, K. Rissanen, C. Bolm, Org. Lett., 2020, 22, 2702-2706.

DOI: 10.1021/acs.orglett.0c00666 (free Supporting Information)



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Abstract

An aza-Michael-addition/cyclization/condensation reaction sequence starting from sulfonimidamides and propargyl ketones provides 1,2,6-thiadiazine 1-oxides. These three-dimensional S,N-heterocycles have been further functionalized by standard cross-coupling reactions, selective bromination of the heterocyclic ring, and conversion into a β-hydroxy substituted derivative.

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Key Words

N-Heterocycles, S-Heterocycles


ID: J54-Y2020