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Published in last 50 years
Racemic sesbanine was synthesized by using regioselective ortho lithiation of N,N-dialkylnicotinamides and subsequent condensation with 3-cyclopentenone as key reactions.
Regioselective ortho lithiation of 2-, 3-, and 4-halopyridines is achieved with lithium diisopropylamide (−78°, tetrahydrofuran) to afford, upon quenching with electrophilic reagents, 2,3- and 3,4-disubstituted pyridines in good to excellent yield.