By A. R. Katritzky, A. J. Boulton
(from preface)The current quantity includes seven chapters, 5 of which take care of features of particular ring platforms: 4-oxy- and 4-keto-l ,2,3,4-tetrahydroiso-quinolines (J. M. Bobbitt), the oxidation items of pyrroles (O. P. Gardini), the pyrindines (4- and 5-azaindenes) (F. Freeman), the NMR spectra of indoles (S. P. Hiremath and R. S. Hosmane), and the 1,2-benzoisothiazole-S-dioxides—(saccharin and its derivatives) (H. Hettler). within the normal box of heterocyclic chemistry, hydrogen trade reactions, as a rule on steel surfaces, are handled (G. E. Calf and J. L. Garnett), and the rest bankruptcy is a scientific evaluate of heterocyclic oligomers (A. Albert and H. Yamamoto). the quantity is devoted to Professor Adrien Albert, and this Preface is by means of a quick biography and bibliography.
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Additional info for Advances in Heterocyclic Chemistry, Vol. 15
Org. Chem. 28, 221 (1963). 113 M. 114 M. Sec. lZOThese biologically significant dimers, which also arise from partial photodestruction of DNA, are thought t o be formed by combination of two radicals (101 and 102), both derived from two molecules of the starting material by the action of lightlZO[Eq. (S)]. e. 121 Similar oxidative dimers were A . J. Varghese, Biochem. Biophys. Res. Commun. 38, 484 (1970). J. Varghese, Biochemistry 9, 4781 (1970). 121 D. J. Anderson, T. L. Gilchrist, and C . W. Rees, Chem.
Base-Catalyzed Oligomerization. Nitriles containing a n active hydrogen atom become dimerized in the presence of sodium ethoxide (the Thorpe reactionzQ). Adipinonitrile, NC(CH2),CN, gives a mixture of the dimer (17; 48% yield) and the trimer (66; 33%) in the presence of sodium ; $ lthe trimer is classified as a type B1 oligomer. It is well known that the addition of ammonia or amines t o nitriles leads to formation of various amidines ; 3 2 this type of oligomerization can be applied to the synthesis of heterocycles.
MihailoviB, and V. Prelog, Helw. Chim. Acta 42, 305 ( 1959). 184H. Erdtman and N. E. Stjernstrom, Acta Chem. Scand. 13, 653 (1959). 185 A. Baeyer, Ber. 15, 50 (1882). 181 See. 1 41 HETEROCYCLIC OLIGOMERS HO (1350) X (135b) X = GO =NH Subclass 2 . Heterocyclic Oligomers from Heterocyclic Monomers a. Acid-Catalyzed Oligomerization. Michael-type addition condensations frequently give oligomers of this type. Well-known examples are the polymerization products of pyrroles and indoles;ls6 the trimer of pyrrole and the dimer of indole have structures 136 and 137, respectively.