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- Title
[3+2] Annulation of 2-substituted 3-nitro-2H-chromenes with mercaptoacetaldehyde: stereoselective synthesis of tetrahydro-4H-thieno[3,2-c]chromen-3-ols.
- Authors
Barkov, Alexey Yu.; Kochnev, Ivan A.; Simonov, Nikita S.; Kutyashev, Igor B.; Zimnitskiy, Nikolay S.; Korotaev, Vladislav Yu.; Sosnovskikh, Vyacheslav Ya.
- Abstract
A diastereoselective method was developed for the synthesis of 4-trifluoromethyl- and 4-phenyl-substituted 3a-nitro-2,3,3a,9b-tetrahydro-4H-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-2H-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-2H-chromenes and in situ generated mercaptoacetaldehyde in Et2O at room temperature over 4–6 h, using Et3N as catalyst.
- Subjects
NITROALDOL reactions; HYDROGEN atom; MICHAEL reaction; ANNULATION
- Publication
Chemistry of Heterocyclic Compounds, 2021, Vol 57, Issue 12, p1204
- ISSN
0009-3122
- Publication type
Article
- DOI
10.1007/s10593-021-03044-9