Synthesis of Thienothiopyranthiones by a New Molecular Rearrangement

On heating with alkynes, the readily prepared 1,3-dithioles 3 undergo a new cycloaddition reaction and an unprecedented molecular rearrangement with loss of chlorine to give the first 7H-thieno[2,3-c]thiopyran-7-thiones 4 and 4H-thieno[3,2-c]thiopyran-4-thiones 5 whose structures were confirmed by X...

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Published inOrganic letters Vol. 7; no. 5; pp. 791 - 794
Main Authors Ogurtsov, Vladimir A, Rakitin, Oleg A, Rees, Charles W, Smolentsev, Alexey A, Belyakov, Pavel A, Golovanov, Denis G, Lyssenko, Konstantin A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.03.2005
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HETEROCYCLES
GENE-EXPRESSION
CHEMISTRY
CHEMOPREVENTION
CANCER
DERIVATIVES
THIOPHENE
DIMETHYL ACETYLENEDICARBOXYLATE
THERMAL REARRANGEMENT
ELECTRON-DENSITY
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Summary:On heating with alkynes, the readily prepared 1,3-dithioles 3 undergo a new cycloaddition reaction and an unprecedented molecular rearrangement with loss of chlorine to give the first 7H-thieno[2,3-c]thiopyran-7-thiones 4 and 4H-thieno[3,2-c]thiopyran-4-thiones 5 whose structures were confirmed by X-ray diffraction. Unexpectedly, the different alkynes used to form 3 and to convert it into 4 and 5 were incorporated regiospecifically into the thiophene and thiopyran rings, respectively.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol0476669