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 comprises seven chapters, 5 of which take care of points of particular ring structures: 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 basic box of heterocyclic chemistry, hydrogen trade reactions, normally on steel surfaces, are handled (G. E. Calf and J. L. Garnett), and the remainder bankruptcy is a scientific evaluate of heterocyclic oligomers (A. Albert and H. Yamamoto). the amount is devoted to Professor Adrien Albert, and this Preface is by way of a quick biography and bibliography.

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YAMAMOTO [Sec. B. , ethyl orthoformate for 116, n = 1 ) . , the 2,2’-ether from N-methylquinolinium chloride,141 also the 2,2’-bispyrazinyl ether142of similar origin. , the tetrasubstituted obtained in high yields by heating chloroethylenes (118;X = CH2,0)144 trifluoroethylene with piperidine and morpholine (respectively) at 80”. 5 mole of an alkylenediamine (in the presence of excess triethylamine) yielded the bisuracilylF. M. Hamer, Qwcrt. Rev. ” Wiley (Interscience), New York, 1964. Hantzsch and M.

And G. P. Nilles, J . Org. Chem. 36, 2486 (1971), and references therein. lo4 Ache~on,~’ p. 114. lo5For a review, see B. R. Brown, Quurt. Rev. 5, 131 (1951). 26 A. ALBERT AND € YAMAMOTO I. [Sec. B. loenoticed that the dimer (82) was formed by amide-like links of the monomer side chains (the desired triazanaphthalene was finally obtained using sodium ethoxide as the catalyst). gNHcoyJ " CONH The dicarboxylic acid (83) was formed as a by-product during the acid from the preparation of 5-hydroxybenzo[b]thiophene-2-carboxylic corresponding amino compound by means of the Bucherer reaction.

The formed by condensation (followedby aerial oxidation)between 7-methylG. Ya. Vanags, Dokl. Akad. NaukSSSR 132,615(1960); Chem. Ab8tr. 54,24636 (1960). J. Brown, “The Pyrimidines,” p. Wiley (Interscience), New York, 1962. 134 A. Albert and E. P. Serjeant, J. Chern. , 3357 (1964). 1 3 2 M. A. Matskanovaand Sec. 1 HETEROCYCLIC OLIGOMERS 33 and 6-methylpterin in 20% sulfuric acid. 135* 136 Some naturally occurring dimeric pteridines have been synthesized similarly (see type B4 oligomers). Many aromatic N-heterocycles add nucleophiles across one or more of the C=N bonds,137thus the adduct (114) is formedes by condensation of barbituric acid (2 moles) and 4-methylpteridine (1 mole) a t pH 2.

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