By A. R. Katritzky, A. J. Boulton
(from preface)Four chapters within the current quantity convey older stories brand new. these at the quinoxalines (Cheeseman and Werstiuk) and on hetero-aromatic quaternization (Zoltewicz and Deady) hold ahead contributions at the similar 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) care for issues formerly lined in different places. The cyclazines, a comparatively new box of chemistry, are reviewed through Flitsch and Kramer, and the azapentaienes— the big variety of nitrogen-containing heterocycles shaped by means of the fusion of 2 fragrant 5-membered rings—are accumulated into one bankruptcy by way of Elguero, Claramunt, and A. J. H. Summers.
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Additional resources for Advances in Heterocyclic Chemistry, Vol. 22
HO 311 Sec. Dl 45 THE PHENANTHROLINES b. N-Oxides. Not unexpectedly, in view of steric difficulties, the claim to the preparation of 1,lO-phenanthrohe 1,10-dioxide3l3now seems to be in error. Two groups have succeeded in obtaining only the mono-No ~ i d eThe . 6. It reacts with benzoyl chloride and potassium cyanide to afford 2-cyano- 1,lO-phenanthroline, the substitution reaction taking precedence over the Reissert reaction. Contrary to previous reports, 1,lO-phenanthroline 1-oxide (82) is nitrated, although with some difficulty, to give 4-nitro- 1,lO-phenanthroline 1oxide (83).
Several . 309 L. R . J. Chem. 43, 1448 (1965). P. Dupois and J. R. Hebd. Seances Acad. , Ser. C 265, 688 (1967). 29v P. Dupois, S. Flandrois, and J. R. Hebd. Seances Acad. , Ser. C 269, 109 1 ( I 969). S. Acker and D. C. S. Patent 3,162,641 (1964) [CA 63, 549 (1965)l. lo’ R . Buvet, P. Dupois, J. Neel, and J. Perichon, Bull. Chim. , 3991 (1969). Io2 S. Flandrois, P. Dupois, P. Delhaes, J. Amiell, and J. Neel, J. Chim. Phys. Physicochim. Biol. 69, 1305 (1972) [CA 77, 157985 (1972)l. Iu3 P. Dupois and J.
Chem. 80,2745 (1958). 315 E. J. Corey, A. L. Borror, and T. Foglia, J. Org. Chem. 30,288 (1965). 316 S. Ogawa and N. Gotoh, Seisan-Kenkyu 22,241 (1970) [CA 73,87818 (1970)l. 317 Z. Dega-Szafran, Rocz. Chem. 46,827 (1972). )I3 46 LINDSAY A. SUMMERS [Sec. 3178 5 . 2,7-Phenanthroline 2,7-Phenanthroline reacts with trimethyloxonium fluoroborate in ethylene chloride solution to give the 2,7-dimethyl diquaternary ~ a l t . ' ~ * From ' ~ ' polarography experiments it was shown to be reduced by a one-electron transfer to the corresponding radical cation.