Premium
A New Synthesis of Sulfur‐, Nitrogen‐ and Oxygen‐Containing Eight‐Membered Ring Lactams
Author(s) -
Pflantz Rebekka,
Sluiter Jonas,
Krička Mario,
Saak Wolfgang,
Hoenke Christoph,
Christoffers Jens
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900825
Subject(s) - chemistry , tetrahydrothiophene , ring (chemistry) , moiety , pyrrolidine , tetrahydrofuran , sulfur , medicinal chemistry , nitrogen , catalysis , lactam , oxygen , organic chemistry , stereochemistry , solvent
Bi(NO 3 ) 3 ‐catalyzed ring expansion of five‐membered ring 1,4‐diketones in the presence of primary amines leads to eight‐membered ring lactams. When applied to starting materials with a tetrahydrothiophene or pyrrolidine moiety, tetrahydro‐2 H ‐1,4‐thiazocin‐3‐ones and hexahydro‐1,4‐diazocin‐2‐ones are obtained as representatives of these very rare heterocyclic systems. In the case of tetrahydrofuran derivatives, other reaction conditions are required and yields of tetrahydro‐2 H ‐1,4‐oxazocin‐3‐ones are very low.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)