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Advances in Heterocyclic Chemistry, Vol. 15 by A. R. Katritzky, A. J. Boulton

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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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.

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