A new class of heterocycles: 1,4,3,5-oxathiadiazepane 4,4-dioxides

This work reports the synthesis of novel 1,4,3,5-oxathiadiazepanes 4,4-dioxides from the reaction of N'-benzyl-N-(2-hydroxyethyl)-sarcosine or proline sulfamide with aromatic aldehydes under acid catalysis. To prepare the starting materials N-Boc-sulfamide derivatives of sarcosine or proline we...

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Published inMolecules (Basel, Switzerland) Vol. 17; no. 2; pp. 1890 - 1899
Main Authors Bendjeddou, Amel, Abbaz, Tahar, Regainia, Zine, Aouf, Nour-Eddine
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 14.02.2012
MDPI
Subjects
Alcohol
Aldehydes
Aldehydes - chemistry
Alkylation
benzodithiazine dioxides
benzoxathiazepine dioxides
cyclic sulfamides
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Magnetic Resonance Spectroscopy
Oxides - chemical synthesis
Oxides - chemistry
Reagents
Sarcosine - chemistry
Spectrometry, Mass, Fast Atom Bombardment
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Summary:This work reports the synthesis of novel 1,4,3,5-oxathiadiazepanes 4,4-dioxides from the reaction of N'-benzyl-N-(2-hydroxyethyl)-sarcosine or proline sulfamide with aromatic aldehydes under acid catalysis. To prepare the starting materials N-Boc-sulfamide derivatives of sarcosine or proline were alkylated with benzyl alcohol under Mitsunobu reaction conditions, the Boc group was removed chemoselectively by acidolysis, and the resulting product reduced to the corresponding alcohol in good yields.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules17021890