Synthesis and Cyclization Reactions of Axially Chiral N-Sulfamoyl-acrylamidines

Synthesis and Cyclization Reactions of Axially Chiral N-Sulfamoyl-acrylamidines

ABSTRACT N‐Sulfonylamines are generated and in situ reacted with 3‐dialkylamino‐2H‐azirines to give N‐sulfamoyl‐acrylamidines. The magnetic nonequivalence of prochiral groups in the 1H NMR spectrum suggests an axially chiral structure, which is supported by density‐functional theory calculations. Ba...

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Veröffentlicht in:Heteroatom chemistry 2014-11, Vol.25 (6), p.619-627
Hauptverfasser: Lender, Andreas, Tornus, Ingo, Hübner, Eike, Schaumann, Ernst
Format: Artikel
Sprache:eng
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Zusammenfassung:ABSTRACT N‐Sulfonylamines are generated and in situ reacted with 3‐dialkylamino‐2H‐azirines to give N‐sulfamoyl‐acrylamidines. The magnetic nonequivalence of prochiral groups in the 1H NMR spectrum suggests an axially chiral structure, which is supported by density‐functional theory calculations. Base‐induced cyclization occurs readily to give 1,2,6‐thiadiazine derivatives.
ISSN:1042-7163
1098-1071
DOI:10.1002/hc.21190