By A. R. Katritzky, A. J. Boulton
(from preface)Four chapters within the current quantity carry older studies modern. these at the quinoxalines (Cheeseman and Werstiuk) and on hetero-aromatic quaternization (Zoltewicz and Deady) hold ahead contributions at the similar matters in Volumes 2 (1963) and three (1964), respectively, of this sequence, whereas these at the phenanthrolines (L. A. Summers) and the isatogens and indolones (Hiremath and Hooper) take care of themes formerly coated in different places. The cyclazines, a comparatively new box of chemistry, are reviewed through Flitsch and Kramer, and the azapentaienes— the wide range of nitrogen-containing heterocycles shaped via the fusion of 2 fragrant 5-membered rings—are gathered into one bankruptcy via Elguero, Claramunt, and A. J. H. Summers.
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3 3 4 A. R. Surrey, A. I. Olivet, and J. 0. Hoppe, J. Am. Chem. 76,4920 (1954). 33s S. F. Mason, J. Chem. ,4874 (1957). 326 327 Sec. I7' With 1 mole of phosphorus pentachloride, the product is 4-chloro-10-hydroxy1,7-phenanthroline (101). This difference in reactivity of the 0x0 groups is almost certainly due to the masking of the 10-0x0 grouping through hydrogen bonding with the 1-nitrogen. With excess of phosphorus oxychloride the 4,lO-dichloro compound 102 is obtained. b. Halogenated 1,7-Phenanthrolines.
Duswalt and M. G . Mellon, Anal. Chem. 33, 1782 (1961). R. L. Eifert and C . S. Hamilton, J. Am. Chem. Soc. 77, 1818 (1955). '61 H. M. Dali, V. N. Gogte, G . B. Mullick, and B. D. Tilak, Indian J. Chem. 12, 1230 164 (1974). 16* K. J. Liska, J. Med. Chem. 15, 1177 (1972). 20 [See. A LINDSAY A. SUMMERS / EtO. CH,,COOEt I TOOEt C (COOEt), CH N‘ H 1. heat 2. hydrolysis ! i I . heat 2. ~~ Extensions of the Conrad-Limpach type of synthesis starting with m-phenylenediamine (20) and utilizing diethyl ethoxymethylene malonate or ethyl ethoxalylacetate, reagents frequently used in quinohe syntheses, have afforded, after hydrolysis, 169 S.
Zh. 20, 526 (1967)[CA 68,105047 (1968)l. 236 J. Moszew and K. Bogdanowicz-Szwed, Zesr. Nauk. Uniw. Jagiellon, Pr. , 234 23s 133 (1970)ICA 74,53590 (1971)l. Y . J. L’Italien and C. K. Banks, J. Am. Chem. 73,3246 (1951). 238 G . Y. S. Patent 3,313,817(1967)[CA 67, 100129 (1967)l. 237 Sec. ”~ Further examples of the Knorr reaction for the synthesis of 3hydroxy-4,7-phenanthrolinesare reported. 232 10-Amino-3-hydroxy-l-methyl-4,7-phenanthroline was obtained similarly from 4-amino-6-acetoacetamidoquinoline.
Advances in Heterocyclic Chemistry, Vol. 22 by A. R. Katritzky, A. J. Boulton