By Alan R. Katritzky
(from preface)The influence of substituents on benzenoid reactivity has been some of the most generally investigated branches of chemistry. The scattered information on pyridine substitution are actually assembled in a evaluation through R. A. Abramovitch and J. G. Saha that is as helpful for exhibiting what is still performed as for what has been accomplished. R. E. Lyle and P. S. Anderson survey reactions of nitrogen heterocycles with complicated hydrides, and the heterocyclic chemistry of nitriles and nitrilium salts is roofed through P. Johnson and R. Madronero.Each of the rest 3 chapters offers with a bunch of compounds: cyclic en amines (K. Blaha and O. Cervinka), pyrazoles (A. N. Kost and that i. I. Grandberg), and physicochemical facets of purines (J. H. Lister).Suggestions are welcome for contributions to extra volumes; they need to be within the kind of a quick synopsis.We thank the Editorial Board, the publishers, and the authors for his or her cooperation.
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Additional info for Advances in Heterocyclic Chemistry
253, 687 (1961). 122 129 Sec. 12s,12' The complexity of this reaction is shown by the fact that adenine gives, in addition to the 5-formamidopyrimidine, some 8-oxoadenine128and small amounts of hypoxanthine, produced by 0x0 displacement of the amino group. 7. Eleetrophilic Subetitution at a Nitrogen Atom In view of the r-electron-excessive character of the imidazole moiety, it is not surprising that electrophilic substitution occurs first at one of the nitrogens in this ring. Further attack is directed to a pyrimidine ring nitrogen.
R. Baker, R. E. Schaub, and J. P. Joseph, J . Org. Chem. 19, 643 (1954). A. Montgomery and H. J. Thomas, J . Am. Chem. Soc. 85, 2672 (1963). 1e2 N. J. Leonard and J. A. Deyrup, J . A m . Chem. SOC. 84,2151 (1962). 163 N. J. Leonard and T. Fuji, J . A m . Chem. SOC. 85,3719 (1963). 1 6 3 ~N. J. Leonard and T. Fuji, Proc. NatZ. Acad. Sci. S. 51,73 (1964). 164 A. Coddington, Bwchim. Biophys. Acta 59,472 (1962). 160 161 J. 42 J. H. LISTER [Sec. 111. 165The unchanged spectra over the whole pH range demonstrates the fixed bond structure.
K. Robins, Can. J . Chem. 41,1807 (1963). 62 63 A. Sec. 6JaThis effect can be related to the mesomeric nature of the chlorine and a degree of bond localization in the pyrimidine moiety with a partial fixation of the C-4-C-5 bond. The combined effect leads to an increased electron density associated with the 2-position. By contrast, 2,6- and 6,8-dichloro- and 2,6,8-trichloropurine undergo normal substitution at the 6-carbon first with this type of reagent. The site of nucleophilic substitution under acid conditions is also decided by the protonated specie formed.