ISSN:
1573-9171
Keywords:
allylboranes
;
triallylborane complexes
;
allylboration
;
pyridines
;
reductivetrans-2,6-diallylation of pyridines
;
cis- andtrans-diallyl-1,2,5,6,-tetrahydropyridines
;
cis- andtrans-2,6-dipropylpiperidines
;
trans-cis-isomerization.
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract The reductivetrans-2,6-diallylation of pyridines with triallyl- and allyl(dialkyl)boranes has been discovered. Heating (40–100 °C) of pyridine, deuteropyridine, or 3-bromopyridine complexes with triallylborane in the presence of alcohols (ROH or CH3OD), water, or Et2NH results in the respectivetrans-2,6-diaIlyl-1,2,5,6-tetrahydropyridines (2,3,22, or25) in 20–97 % yields. A preparative method for the isomerization oftrans-2,6-diallyl compounds2 and25 into the respectivecis-isomers4 and28 by heating them with triallyl- or allyl(dialkyl)boranes (125–150 °C) has been suggested. The hydrogenation oftrans- orcis-2,6-diallyl-1,2,5,6-tetrahydropyridines gavetrans- orcis-2,6-dipropylpiperidines, respectively. Thecis- andtrans-configurations of compounds2 and4 were established by analyzing the NMR spectra ofN-benzyl (7 and13) andN,N-dimethyl (6 and 14) derivatives of piperidine derivatives5 and8. A possible mechanism for the reductive diallylation of pyridines has been discussed.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00699842
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