By Alan R. Katritzky
(from preface)The impression of substituents on benzenoid reactivity has been some of the most generally investigated branches of chemistry. The scattered information on pyridine substitution at the moment are assembled in a evaluate by way of R. A. Abramovitch and J. G. Saha that is as worthy for exhibiting what is still performed as for what has been completed. R. E. Lyle and P. S. Anderson survey reactions of nitrogen heterocycles with advanced hydrides, and the heterocyclic chemistry of nitriles and nitrilium salts is roofed by means of P. Johnson and R. Madronero.Each of the rest 3 chapters bargains with a gaggle 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 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 info for Advances in Heterocyclic Chemistry
Summary . . . . . . . . 87 88 89 89 90 91 93 The reactions of complex metal hydrides occur by an attach of the nucleophilic hydride ion on an electrophilic center. Aromatic nitrogen heterocycles in which the nitrogen has contributed only one electron to the n-system (1) are electrophilic as compared with benzene, and have been shown to undergo reduction by the active reducing agent, lithium aluminum hydride. The nitrogen heterocycles in which the heteroatom has contributed two electrons to the n-system (2) are electron-rich as compared with benzene and usually do not undergo reaction by reduction with complex metal hydrides.
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.
Schachter, J . Am. Pharm. Assoc. 43, 619 (1954). Biltz and J. Sauer, Ber. Deut. Chem. Ges. 64, 752 (1931). Brunner and H. Leins, Ber. Deut. Chem. Ges. 30, 2584 (1897). 121 J. Jones and R. K. Robins, J . Am. Chem. SOC. 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.