By A. R. Katritzky, A. J. Boulton
(from preface)Four chapters within the current quantity carry older experiences brand new. these at the quinoxalines (Cheeseman and Werstiuk) and on hetero-aromatic quaternization (Zoltewicz and Deady) hold ahead contributions at the related 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 means of Flitsch and Kramer, and the azapentaienes— the wide range of nitrogen-containing heterocycles shaped via 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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Extra info for Advances in Heterocyclic Chemistry, Vol. 22
Dwyer, R. D. Wright, and A. Shulman, Australian Patent 251,598 (1964) [CA 66,46417 (1967)l. 293 S. Ogawa, T. Nakajima, and N. Gotoh, Seisan-Kenkyu 21, 474 (1969) [CA 73, 1309 13 (1 970)l. 294 E. J. Gabbay, R. E. Scofield, and C. S. Baxter, J . Am. Chem. 95,7850 (1973). 295 S. Minami, Y. Takase, and S. Yamabe, Japanese Patent 49,798 (1973) [CA 79, 105230 (1973)l. 296 J. A. Zoltewicz, and L. W. Deady, J . Am. Chem. 94,2765 (1972). 291 292 Sec. 303 Because of steric difficulties, it has not been found possible to obtain simple alkyl diquaternary salts of 1,lO-phenanthroline.
Chem. 10, 353 (1973).
The parent compound forms quaternary salts with phenacyl bromides and b r o m o a ~ e t o n e . ~ ~ ~ Various symmetrically substituted polymethyl 1,lO-phenanthrolines have been quaternized with a variety of alkyl With unsymmetrically substituted 1,10-phenanthrolines, it is not always clear which nitrogen has been quaternized, and the structure of the products sometimes remains u n ~ e r t a i n . 2-Chloro~ ~ ~ . ~ ~1,lO-phenanthroline ~ (as), however, is quaternized in the 10-position to give (70), the structure of the product being proved by oxidation to 2-chloro-9,lO-dihydro- 10-methyl9-0x0- 1,lO-phenanthroline (7 1) with potassium f e r r i ~ y a n i d eA .
Advances in Heterocyclic Chemistry, Vol. 22 by A. R. Katritzky, A. J. Boulton