[3+2] Annulation of 2-substituted 3-nitro-2H-chromenes with mercaptoacetaldehyde: stereoselective synthesis of tetrahydro-4H-thieno[3,2-c]chromen-3-ols

A diastereoselective method was developed for the synthesis of 4-trifluoromethyl- and 4-phenyl-substituted 3a-nitro-2,3,3a,9b-tetrahydro-4 H -thieno[3,2- c ]chromen-3-ols having cis configuration of substituents at the C-3, C-3a, C-4 atoms and the 9b-CH hydrogen atom from the available starting mate...

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Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2021-12, Vol.57 (12), p.1204-1211
Main Authors: Barkov, Alexey Yu, Kochnev, Ivan A., Simonov, Nikita S., Kutyashev, Igor B., Zimnitskiy, Nikolay S., Korotaev, Vladislav Yu, Sosnovskikh, Vyacheslav Ya
Format: Article
Language:English
Subjects:
Cascade chemical reactions
Chemical reactions
Chemistry
Chemistry and Materials Science
Hydrogen
Organic Chemistry
Pharmacy
Room temperature
Stereoselectivity
Substitutes
Synthesis
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Summary:A diastereoselective method was developed for the synthesis of 4-trifluoromethyl- and 4-phenyl-substituted 3a-nitro-2,3,3a,9b-tetrahydro-4 H -thieno[3,2- c ]chromen-3-ols having cis configuration of substituents at the C-3, C-3a, C-4 atoms and the 9b-CH hydrogen atom from the available starting materials – 3-nitro-2 H -chromenes and 2,5-dihydroxy-1,4-dithiane in 80–92% yields. This approach relied on a tandem of Michael and Henry reactions between 3-nitro-2 H -chromenes and in situ generated mercaptoacetaldehyde in Et 2 O at room temperature over 4–6 h, using Et 3 N as catalyst.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-021-03044-9