Regular Issue

Vol. 26, No. 8, 1987

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Review | Regular issue | Vol 26, No. 8, 1987, pp. 2223 - 2246
Published online:
DOI: 10.3987/R-1987-08-2223
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


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.

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Review | Regular issue | Vol 26, No. 8, 1987, pp. 2247 - 2265
Published online:
DOI: 10.3987/R-1987-08-2247
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.


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.

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32 data found. 31 - 32 listedFirst Previous