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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POPP [SEC. Iv. D. 40I n benzene solution, using a high-pressure mercury source, the yield of nitrile was lower. The photolyses also produced a low yield of the aldehydic fragment corresponding t o the aroyl group. Photolysis of the quinoline Reissert compound (7)showed a marked dependence on the wavelength of the ultraviolet source. With 2537 A light in acetonitrile an 8 yoyield of 2-cyanoquinoline and a trace of benzaldehyde were obtained, while with a high-pressure source and benzene as a solvent a 41 yoyield of the dimer (48) was obtained as the only identifiable p h o t o p r o d ~ c t .

32 c. 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.

54 L. R. Walters, J . Chem. Eng. Data 10, 79 (1965). 52 53 SEC. v. l’. 48It has been postulated that the initial dehydration converts 55 t o 59, an intermediate analogous to that (12) proposed for the hydrolysis of normal Reissert compounds. l The reaction of quinoline, benzoyl chloride, and silver phenylacetylide led to the formation of 6055which could be considered as a t & IC e CeH5-C=O (60) 55 H 5 Q,,6H5 I Ce&-C=O (61) T. Agawa and S. I. Miller, J . Am. Chem. SOC. 83, 449 (1961). 22 F. D. POPP [SEC.

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