By A. R. Katritzky, A. J. Boulton
(from preface)Four chapters within the current quantity convey older reports brand new. these at the quinoxalines (Cheeseman and Werstiuk) and on hetero-aromatic quaternization (Zoltewicz and Deady) hold ahead contributions at the comparable topics 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 subject matters formerly lined somewhere else. The cyclazines, a comparatively new box of chemistry, are reviewed by way of Flitsch and Kramer, and the azapentaienes— the wide range of nitrogen-containing heterocycles shaped by means of the fusion of 2 fragrant 5-membered rings—are accumulated into one bankruptcy by means of Elguero, Claramunt, and A. J. H. Summers.
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Additional resources for Advances in Heterocyclic Chemistry, Vol. 22
Heterocycl. Chem. 9, 1021 (1972). 264 A. Schoenberg and G. Schuetz, Chem. Ber. 95,2386 (1962). 265 A. Schoenberg, E. Schulze-Pannier, and H. Schwarz, Chem. Ber. 108, 263 322 (1975). F. H. Case, J. Heterocycl. Chem. 4,157 (1967). 267 F. H. Case, J. Org. Chem. 30,93 1 (1 965). W. Rothkopf, D. Woehrle, R. Mueller, and G. Kossmehl, Chem. Ber. 108, 875 266 (1975). 269 W. Ried and E. Torok,Liebigs Ann. Chem. 687, 187 (1965). F. Feigl and D. Goldstein, Z . Anal. Chem. 178,265 (1961). Sec. Cl THE PHENANTHROLINES 37 4,7-Phenanthroline-5,6-dioneforms a dioxime that is advocated as a derivative suitable for its analytical e ~ t i m a t i o n .
C. Ennis, Aust. J. Chem. 16,840 (1963). , Netherlands Patent 6,4 10,619 (1965) [CA 63,9946 (196511. *08E. Samuel and W. G. C. Raper, Australian Patent 261,910 (1965) [CA 69, 10426 (1968)l. In4 26 LINDSAY A. SUMMERS [Sec. '* E. 2,7-PHENANTHROLINE S The first synthesis of 2,7-phenanthroline (5) was accomplished in 1966 by Perkampus and Kassebeer,'* who obtained it in 23% yield by irradiating trans- 1-(2-pyridyl)-2-(4-pyridyl)ethylene for several hours in in 45% yield by a benzene solution. It was obtained ~ubsequently~~ Skraup reaction on 7-aminoisoquinoline (33) (which was erroneously termed 7-aminoquinoline in the original paper).
P. Weatherhead,J. Chem. , 1164 (1940). E. H. Woodruff and R. Adams,J. Am. Chem. 54, 1977 (1932). 241 J. E. A. Otterstedt and R. Pater, J. Heterocycl. Chem. 9,225 (1972). 239 240 32 LINDSAY A. SUMMERS [Sec. A (42) to 4,7-bis-2'-cyanoethyl- 1,2,3,4,7,8,9,10-octah ydro- 1,10-dioxo-4,7phenanthroline (43) with aluminum chloride and hydrochloric acid in c h l o r o b e n ~ e n eThe . ~ ~ ~structure was confirmed spectroscopically and by reaction with hydrazine, which gave the tetraazapyrene derivative (44).