By A. R. Katritzky, A. J. Boulton
(from preface)Four chapters within the current quantity carry older studies brand new. these at the quinoxalines (Cheeseman and Werstiuk) and on hetero-aromatic quaternization (Zoltewicz and Deady) hold ahead contributions at the comparable 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 subject matters formerly coated in other places. The cyclazines, a comparatively new box of chemistry, are reviewed via Flitsch and Kramer, and the azapentaienes— the big variety of nitrogen-containing heterocycles shaped via the fusion of 2 fragrant 5-membered rings—are amassed into one bankruptcy via Elguero, Claramunt, and A. J. H. Summers.
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Extra resources for Advances in Heterocyclic Chemistry, Vol. 22
W. S. Waring, German Patent 2,220,294 (1972) [CA 78,29744 (197311. R. L. Shivalkar and S. V. Sunthankar, J. Sci. Znd. Res. (Zndiu) 188,447 (1959). S . Minami, M. Nakata, and M. Shimizu, Japanese Patent 55,698 (1974) [CA 82, 156249 (1975)l. , British Patent 1,147,760 (1969) [CA 71,49967 (1969)l. S. K. Khetan and M. V. George, Can. J. Chem. 47,3545 (1969). 173 22 [Sec. A LINDSAY A. SUMMERS fused structure was preferred over the alternative linearly fused one on NMR and IR evidence. p-Phenylenediamine, however, under similar conditions, gave a diazaanthracene rather than a 4,7-phenanthroline.
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. As expected, halogen substituents ortho and para to the ring nitrogens in phenanthrolines are usually readily replaced by nucleophiles.
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.