HETEROCYCLES
An International Journal for Reviews and Communications in Heterocyclic ChemistryWeb Edition ISSN: 1881-0942
Published online by The Japan Institute of Heterocyclic Chemistry
Regular Issue
Vol. 26, No. 8, 1987
Published online:
■ Synthesis and Reactions of N-Substituted 2(1H)-Pyrimidinones and Pyrimidinethiones
Akira Katoh, Takehiko Nishio, and Choji Kashima
*Department of Chemistry, University of Tsukuba, 1-1-1 Ten-nodai, Tsukuba-shi, Ibaraki, 305-8571, Japan
Abstract
The synthesis of N-substituted 2(1H)-pyrimidinanes and pyrimidinethiones bearing various substituents is discussed. The regioselective substitution of C-6 methyl protons of N-substituted 4,6-dimethyl-2(1H)-pyrimidinones is observed by the treatment with electrophiles such as alkyl halides and benzenediazonium salt. The ring transformations to benzene, isoxazole, pyrazole, triazole, pyridine, and pyrimidine by the reaction of title compounds with a variety of nucleophiles are reviewed. Dihydra- and tetrahydro-2(1H)- pyrimidinones and the corresponding thiones are regiaselectively obtained by reaction with organometallic reagents and metal hydride complexes. The photochemical behaviors of N-substituted 2(1H)-pyrimidinones are also reviewed.
Published online:
■ Synthetic Strategies for the Construction of 3-Pyrrolidinol, a Versatile Nitrogen Heterocycles
Denise M. Flanagan and Madeleine M. Joullié
*Department of Chemistry, 231 South 34th Street Philadelphia, PA 19104-6323, U.S.A.
Abstract
The biological and/or commercial importance of molecules containing the-3-pyrrolidinol nucleus are presented. Synthetic strategies for preparing both racemic and chiral 3-pyrrolidinols and their N-substituted derivatives ere described. A comparison of the yields and optical purities of the chiral products is also given.