Advances in Heterocyclic Chemistry, Vol. 22 by A. R. Katritzky, A. J. Boulton

By A. R. Katritzky, A. J. Boulton

(from preface)Four chapters within the current quantity convey older studies modern. 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 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 amassed into one bankruptcy by means of Elguero, Claramunt, and A. J. H. Summers.

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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). '~ IV. General Reactions A. REDUCTION 1. IJO-Phenanthroline The reduction of 1,lO-phenanthroline (4) occurs preferentially in the pyridine rings.

1,5-Diazafluorenone (3%) is a byproduct. ^" 2. 1 ,g-Phenanthroline Unlike 1,7-, 1,lo-, and 4,7-phenanthrolines, which give nitrated products, the predominant product of the reaction of 1,8-phenanthroline (2) with mixed nitric and sulfuric acids is the 5,6-dione (59) (28%). Both the 5-nitro- (60) and 6-nitro- 1,8-phenanthrolines (61) are formed, but in much lower yield (-6-7%). 252Bromination of 1,8-phenanthroline affords the 5 - and 6bromo derivatives and the 5,6-dibromo 271 I. S. Tubina and E.

The other product was the 7,8,9,10-tetrahydro derivative resulting from the hydrogenation of the unsubstituted ring. 'O' With finely divided platinum as catalyst, 4,7-phenanthroline is hydrogenated at near atmospheric pressure. Although a mixture of products was formed, only the 1,2,3,4-tetrahydro derivative was The chemical reduction of 4,7-phenanthroline has been re-examined. 246In the course of the structural verification of these products, it has been found246that the compound previously to be 3,8dioxo- 1,2,3,4,7,8,9,10-0ctahydro-4,7-phenanthroline(49) is in fact the linear diazaanthracene isomer (50) and the derived octahydro cornpound reported by Smith and y~~~~ is likewise a diazaanthracene derivative.

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