Synthesis of (+/-)-8-Oxa-3-azabicyclo[3.2.1]octan-2-thione and (+/-)-2-Oxa-5-azabicyclo[2.2.1]heptan-6-thione: Potential Synthons for the Preparation of Novel Heteroaryl-Annulated Bicyclic Morpholines

The bridged bicyclic morpholinethiones (+/-)-8-oxa-3-azabicyclo[ 3.2.1]octane-2-thione and (+/-)-2-oxa-5-azabicyclo[2.2.1]heptane-6-thione have been prepared in five and eight steps, respectively. Both compounds were derived from a respective requisite cis-disubstituted tetrahydrofuran, which was st...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 7; pp. 1113 - 1119
Main Authors Walker, Daniel P., Wishka, Donn G., Beagley, Paul, Turner, Gemma, Solesbury, Nicola
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.04.2011
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FURAN
bicyclic compounds
heterocycles
hydrogenation
stereoselective synthesis
furans
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Summary:The bridged bicyclic morpholinethiones (+/-)-8-oxa-3-azabicyclo[ 3.2.1]octane-2-thione and (+/-)-2-oxa-5-azabicyclo[2.2.1]heptane-6-thione have been prepared in five and eight steps, respectively. Both compounds were derived from a respective requisite cis-disubstituted tetrahydrofuran, which was stereoselectively prepared via hydrogenation of the corresponding disubstituted furan derivatives.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0030-1258464