Reactions of Cyanomethanesulfonamides with Aldehydes and Synthesis of 2-Benzyl-2,3-dihydrobenzopyrano[3,2-e] [1,2,4]thiadiazine 1,1-Dioxides |
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Authors: | Martin Winterwerber Rouzita Geiger Ursula Predoiu Hans-Hartwig Otto |
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Affiliation: | (1) Department of Pharmaceutical/Medicinal Chemistry, Institute of Pharmacy, University of Greifswald, Greifswald, Germany;(2) Institute of Pharmacy, University of Freiburg, Freiburg, Germany |
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Abstract: | Summary. Reactions of cyanomethanesulfonamides with aromatic aldehydes in the presence of AcOH and piperidine produced the addition products, the 1-cyano-2-arylethenesulfonamides, whereas reactions with benzonitrile yielded the 2-amino-1-cyano-2-phenylethenesulfonamides only when done in THF with BuLi. No addition products were isolated from the analogue reactions with 2-hydroxybenzaldehyde (salicylaldehyde). Instead, we obtained 2-imino-2H-chromene-3-sulfonamides with good to excellent yields. These 2H-chromene derivatives allowed a number of transformations, from which the reactions with orthoformates opened an approach to the hitherto unknown benzopyrano[3,2-e] [1,2,4]thiadiazine ring system. |
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Keywords: | . Cyanomethanesulfonamide Aldehyde Condensation Cyclization Benzopyrano[3,2-e] [1,2,4]thiadiazine 1,1-dioxide. |
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