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Synthesis 2007(24): 3831-3838
DOI: 10.1055/s-2007-990892
DOI: 10.1055/s-2007-990892
PAPER
© Georg Thieme Verlag Stuttgart · New York
Thiourea to Dithiazolopyrimidines: Highly Regio- and Stereoselective Synthetic Routes via Mercaptoacetylative Cyclization
Further Information
Received
31 August 2007
Publication Date:
15 November 2007 (online)
Publication History
Publication Date:
15 November 2007 (online)
Abstract
The Michael addition of 3-imino-1,4,2-dithiazoles to 4-arylidene-1,3-oxathiolan-5-one afforded isolable adducts regio- and diastereoselectively, which underwent mercaptoacetylative annulation of the mercaptopyrimidine ring onto the dithiazole under solvent-free microwave irradiation conditions. Alternatively, similar conjugate addition of [(methylsulfinyl)methyl]isothioureas to 4-arylidene-1,3-oxathiolan-5-one diastereoselectively afforded Michael adducts that underwent mercaptoacetylative ring transformation followed by heterocyclization via deoxygenative demethylation with thionyl chloride to yield the same products, 7-aryl- or 2,7-diaryl-6,7-dihydro-6-mercapto-5H-[1,4,2]dithiazolo[2,3-a]pyrimidin-5-ones, regio- and diastereoselectively.
Key words
microwaves - thiourea - diastereoselective synthesis - mercaptodithiazolopyrimidines - Michael addition
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