By Alan R. Katritzky
(from preface)The influence of substituents on benzenoid reactivity has been essentially the most commonly investigated branches of chemistry. The scattered information on pyridine substitution are actually assembled in a overview by way of R. A. Abramovitch and J. G. Saha that's as useful for displaying what continues to be 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 by means of P. Johnson and R. Madronero.Each of the remainder 3 chapters bargains 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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Extra resources for Advances in Heterocyclic Chemistry
This tautomer, although NLE calculations show it to have the most electrophilic carbon at the 8-position,'1° has a debatable existence in this reaction. With 7-methylhypoxanthine, in which intramolecular hydrogen-bonding of this type cannot exist, oxidation occurs first a t the 2-position. Similar configurational considerations may explain the fact that rat liver enzymes convert purine to uric acid'" in the reverse order of oxidation to that obtained with xanthine oxidase, substitution occurring first at the 8- then at the 2- and 6positions.
Kwietny, G. Levin, and D. J. Brown, J . Am. Ghem. SOC. 82, 598 (1960). 103 F. Bergmann and S. Dikstein, J . Biol. Chem. 223, 765 (1956). 104 F. Bergmann, H. Ungar, and A. Kalmus, Biockim. Biophya. Acta 45, 49 102 (1960). M. Perrault, C. Valdemoro and B. Pullman,J. Theoret. B i d . I, 180 (1961). 28 J. H. LISTER [Sec. 111. which in this case may bear some relationship to the true electronic state of the molecule as the enzyme reactions take place under near neutral conditions. Nevertheless, the possibility of modification of the electron distribution in the purine, due to the interaction with the receptor surface, must also be borne in mind.
Consequently, if the stereospecific requirements are not satisfied, further oxidation is inhibited. 113I n contrast, both 7- and 9-methylpurine are readily oxidized to their hypoxanthine analogs but are resistant to further treatment,lo2* lo3 as are the corresponding methylated xanthine homologs. 6. Electrophilic Substitution at a Carbon Atom Electrophilic substitution is possible at either a carbon or a nitrogen atom. However, of the two sites, from both a chemical and a biological standpoint, the more important reactions involve the heteroatom.