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Download Advances in Heterocyclic Chemistry, Vol. 9 by A.R. Katritzky, A.J. Boulton (Eds.) PDF

By A.R. Katritzky, A.J. Boulton (Eds.)

(from preface)The 9th quantity of Advances in Heterocyclic Chemistry contains surveys of the chemistry of the next teams of heterocyclic compounds: 1,2,5-thiadiazoles (L. M. Weinstock and P. I. Pollack); 1,3,4-thiadiazoles (J. Sandstrom); pyridazines (M. Tisler and B. Stanovnik); Reissert compounds (F. D. Popp); phenothiazines (C. Bodea and that i. Silberg); and pyrrolopyridines (R. E. Willette).Suggestions are welcomed for contributions to destiny volumes; they need to be within the type of brief synopses.Thanks are as a result of Editorial Board, the writer, and the authors for his or her cooperation.

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Robinson, J . Chem. SOC. 125, 626 4 5 (1924). M. Patterson, L. T. Capell, and D. F. , p. 166. Am. Chem. , 1960. 10 A. A. loa The editors of the Journal of the Chemical Xociety prefer to use the diazaindene nomenclature, according to which compound 2 is 1,7diazaindene, etc. I n the present review the azaindole nomenclature is used. I n addition to being the most widely adopted and more concise, i t lends to a more convenient method of naming azalogs of known compounds, such as 7-azatryptophan. (3) (4) 111.

61 Under normal Fischer indolization conditions, the pyridine ring is protonated or associated with the metal ion, deactivating it for the electrophilic cyclizatioii stage of the reaction. QJo H QqJJ \ (41, n = 1, 2) a general discussion of the mechanism of this reaction see R. Robinson, Chem. Rev. 63,372 (1963). 61 For 42 R. E. 111. D. 5 yo yield from isobutyraldehyde 4pyridylhydrazone, obtaining none of the expected 3,3-dimethyl-5azaindolenine. 5% yield. There is no evidence to date to support either structure.

Reaction of 8 with carbon disulfide and sodium hydride in dimethylformamide a t room temperature gave only unchanged 8 and not 1-isoquinolyl phenyl ketone as might have been expected if 20 did not react with carbon disulfide. 27 44 L. R. Walters, E. G. Podrebarac, and W. E. McEwen, J . Ory. Chem. 26, 1161 (1961). 17 REISSERT COMPOUNDS S II SCH3 (42) Use of 7 in the above reaction sequence did not lead to a product analogous to 42 but rather to 43, providing a second example of the . ~ ~formation of 43 can be rationreaction of 19 in the 4 - p o ~ i t i o nThe alized by the removal of a proton from intermediate 44 followed by reaction with methyl iodide.

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