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Organocatalyzed Thia‐Michael Addition and Sequential Inverse Electron Demanding Diels‐Alder Reaction to 3‐Vinyl‐1,2,4‐ triazine Platforms
Author(s) -
Berthonneau Clément,
Buttard Floris,
Hiebel MarieAude,
Suzenet Franck,
Brière JeanFrançois
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700831
Subject(s) - chemistry , nucleophile , inverse , michael reaction , triazine , propargyl , diels–alder reaction , organic chemistry , catalysis , combinatorial chemistry , medicinal chemistry , mathematics , geometry
This work highlights the use of 3‐vinyl‐1,2,4‐triazines as original thia‐Michael acceptors and inverse electron demanding Diels‐Alder platforms en route to new 7,8‐dihydro‐5 H ‐thiopyrano[4,3‐ b ]pyridines. The required but rather unstable propargylthiol nucleophiles were successfully generated in‐situ upon an innovative DBU‐catalyzed methanolysis event of the corresponding propargyl thioacetate derivatives.