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Regioselective addition of n-alkyllithiums to alpha,alpha '-disubstituted-1,8-naphthyridines: Synthesis of 6-amino-3-pyridinol analogs of alpha-tocopherol

Title
Regioselective addition of n-alkyllithiums to alpha,alpha '-disubstituted-1,8-naphthyridines: Synthesis of 6-amino-3-pyridinol analogs of alpha-tocopherol
Author
남태규
Keywords
1,8-naphthyridine; alkyllithium; chelation; solvent effects; alpha-tocopherol
Issue Date
2005-06
Publisher
GEORG THIEME VERLAG KG
Citation
SYNTHESIS-STUTTGART, v. 9, Page. 1397-1404
Abstract
n-Alkyllithiums were added to alpha,alpha'-disubstituted-1,8-naphthyridines in non-polar solvents Such as Et2O-hexane mixtures. In polar solvents such as THF, alkyllithium acts as a base rather than a nucleophile. Regioselective addition was achieved for substrates capable of five-membered cyclic chelation of the (alkyl)lithium reagent. Substrates with a TBS-protected alcohol as the co-chelating moiety afforded the best combination of yield and regioselectivity. This methodology was Successfully employed in the preparation of two 6-amino-3-pyridinol analogs of pentamethyl-chromanol (PMC), an alpha-tocopherol derivative with its isoprenoid side chain truncated to a methyl group.
URI
https://www.thieme-connect.com/products/ejournals/html/10.1055/s-2005-865308http://repository.hanyang.ac.kr/handle/20.500.11754/111093
ISSN
0039-7881; 1437-210X
DOI
10.1055/s-2005-865308
Appears in Collections:
COLLEGE OF PHARMACY[E](약학대학) > PHARMACY(약학과) > Articles
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