By Alan R. Katritzky
(from preface)The influence of substituents on benzenoid reactivity has been probably the most largely investigated branches of chemistry. The scattered facts on pyridine substitution at the moment are assembled in a overview through R. A. Abramovitch and J. G. Saha that's as invaluable 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 via P. Johnson and R. Madronero.Each of the rest 3 chapters offers with a gaggle of compounds: cyclic en amines (K. Blaha and O. Cervinka), pyrazoles (A. N. Kost and that i. I. Grandberg), and physicochemical points of purines (J. H. Lister).Suggestions are welcome for contributions to additional volumes; they need to be within the kind of a brief 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
8 3 E. N. Shaw, J . A m . Chern. SOC. 80,3899 (1958). 84 R. H. Lindsay, W. H. Paik, and P. P. Cohen, Biochim. Biophya. Acta 58,585 81 82 (1962). A. Albert and D. J. Brown, J . Chem. SOC. 1954, 2060. 86 J. A. Montgomery and C. Temple, J . Am. Chem. SOC. 79, 5238 (1957). 85 Sec. 1 23 PHYSICOCHEMICAL ASPECTS OF PURINES further attack. The presence of even traces of methanol in this reaction, if carried out a t room temperature, leads to preferential formation of 6 - m e t h o x y p ~ i n e . ~ ' The instability of simple purine ribosides toward alkaliAs-89 can be related to the fairly strong electron-withdrawing power of the ribose moiety, which directs the nucleophile to the 8-carbon.
82, 3773 (1960). Shapiro, J . Am. Chem. SOC. 86, 2948 (1964). 119 32 J. H. LISTER [Sec. 111. electron-deficient character of the %carbon atom, this reaction is proposed to occur via a nucleophilic substitution by nitrite ion of the diazonium group. 121a Another route (69-+68) producing 8-nitropurines was initially considered to have given 8-nitrosopurines,l l 9but these were shown later to be mixtures of 8-nitropurines and starting material121; here an 8-thione group (69) undergoes electrophilic substitution by a nitronium ion.
Gulland and L. F. Storey, J . Chem. Soc. 1938, 692. 79 H. C. Koppel and R. K. Robins, J . Am. Chem. SOC. 80, 2751 (1958). 80 R. M. Cresswell and G. B. Brown, J . Org. Chem. 28, 2560 (1963). 77 78 J. H. LISTER 22 [Sec. 111. H (35) 4. Nueleophilic Substitution Leading to Degradation or Rearrangement a. Degradation. ~~ imidazole derivatives. s4 Stability toward alkali is a feature of 0x0 derivatives and purines containing electron-releasing groups, while N-alkylation, which may prohibit anion formation, has the opposite effect.
Advances in Heterocyclic Chemistry by Alan R. Katritzky