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2005
Pyridine derivatives
R 0380
Synthesis of 3-Arylpiperidines by a Radical 1,4-Aryl Migration. — The key step
the new route involves a 1,4-radical migration of an aryl group present in sulfon37- 139 of
amides such as (II) from sulfur to carbon in the presence of isopropanol as hydrogen
atom donating solvent to afford β-arylacetamides. The electronic nature of the aryl
group does not affect greatly the yield of this rearrangement. Acid hydrolysis and subsequent cyclization of the migration products affords the desired piperidines. The approach to aryl-substituted piperidines is expanded by exposure of recently prepared
compound (IX) to ammonia or primary amines. — (GHEORGHE, A.;
QUICLET-SIRE, B.; VILA, X.; ZARD*, S. Z.; Org. Lett. 7 (2005) 8, 1653-1656;
Lab. Synth. Org., CNRS, DCSO, Ec. Polytech., F-91128 Palaiseau, Fr.; Eng.) —
Klein
2005
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