Synthesis of 3,4-Dihydro-2H-Thiopyrans and Thiopyrano[3,4-c]Chromenes Having a 1,2,3-Triazole Substituent by Using Thionylation - Hetero-Diels-Alder Domino Reaction

We have developed a thionylation - hetero-Diels-Alder domino reaction using alpha,beta-unsaturated ketones with 1,2,3-triazole substituents, namely, 3-[2-(allyloxy)phenyl]-1-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-prop-2-en-1-ones, leading to 3,4-dihydro-2De-thiopyranes and thiopyrano[3,4-N]chromeno...

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Published inChemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 50; no. 4; pp. 544 - 549
Main Authors Pokhodylo, N. T., Savka, R. D., Obushak, M. D.
Format Journal Article
LanguageEnglish
Published NEW YORK Springer Nature 01.07.2014
Springer
Subjects
Chemistry
Chemistry, Organic
Diels-Alder reaction
Heterocyclic aromatic compounds
Physical Sciences
Resveratrol
Science & Technology
thionylation
SULFIDES
thiopyran
thiopyrano[3,4-c]chromene
1,2,3-triazole
domino reaction
hetero-Diels-Alder reaction
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Summary:We have developed a thionylation - hetero-Diels-Alder domino reaction using alpha,beta-unsaturated ketones with 1,2,3-triazole substituents, namely, 3-[2-(allyloxy)phenyl]-1-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-prop-2-en-1-ones, leading to 3,4-dihydro-2De-thiopyranes and thiopyrano[3,4-N]chromenones. Variants of intra- and intermolecular cycloaddition were studied, as well the stereo- and regioselectivity of such reactions was assessed.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-014-1505-4