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Selective, one‐pot synthesis of 2,3,6‐trisubstituted pyridine and 2‐cyclohexen‐1‐one derivatives from bicyclic ketals
Author(s) -
Jun JongGab,
Ha Tae Hee
Publication year - 1997
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570340151
Subject(s) - chemistry , pyridine , bicyclic molecule , nitrile , reagent , boron trifluoride , organic chemistry , benzoyl chloride , octane , trimethylsilyl trifluoromethanesulfonate , lewis acids and bases , methylene , medicinal chemistry , catalysis
Boron difluoromethanesulfonate, prepared from 5 equivalents of trimethylsilyl methanesulfonate and 1 equivalent of boron trifluoride etherate, has proved to be an active Lewis acid catalyst for the one‐pot transformation reaction of bicyclic ketals in the 6,8‐dioxabicyclo[3.2.1]octane series to 2,3,6‐trisubstituted pyridine or 2‐cyclohexen‐1‐one selectively, depending on conditions. A 1,5‐diketone was the reaction intermediate for both products. Pyridine was formed selectively by using a nitrile as a solvent or a reagent, but cyclohexenone was prepared in methylene chloride instead of a nitrile.