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By C. F. H. Allen

Content material:
Chapter I Azaanthracenes (pages 14–164): C. V. Wilson
Chapter II Azaphenanthrenes (pages 165–215): John R. Thirtle
Chapter III 4?Azaphenanthrenes (pages 216–270): J. A. Van Allan
Chapter IV 5?Azaphenanthrenes (pages 271–319): J. A. Van Allan
Chapter V Diazaphenanthrenes (Except Phenanthrolines) (pages 320–385): John R. Thirtle
Chapter VI 1,10?, 1,7?, and 4,7?Diazaphenanthrenes (pages 386–456): Bruce Graham
Chapter VII different Polyazaphenanthrenes (pages 457–483): John R. Thirtle
Chapter VIII Azabenzonaphthenes (pages 484–550): James H. Richmond
Chapter IX The Ultraviolet Absorption Spectra of Polycyclic Heterocyclic fragrant Compounds (pages 551–566): G. M. Badger
Chapter X Naphthalimides: Addendum (pages 567–569): C. F. H. Allen

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Additional resources for Chemistry of Heterocyclic Compounds: Six Membered Heterocyclic Nitrogen Compounds with Three Condensed Rings, Volume 12

Example text

U3 \ (=I) (VIII) \Br /\/ (LXII) (3)Nitration. Nitration of the parent compound is not reported, no doubt because of its difficult accessibility. 9-Chloro-I-azaanthracene (VIII) yields a mixture of the 5-(LXIII) and 8-(LXIV) nitro derivatives (the former in the larger proportion21)when the nitration is carried out with concentrated nitric acid (spgr. 49) at -18". > \/\//\' (LSIII) c;cc] NO, c1 (LXIV) Under entirely different nitrating conditions (in acetic acid at looo), 9-chloro-10-nitro-I-azaanthracene(LXV) is formed in 70 yo yield33; its orientation is established by its oxidation to I-azaanthraquinone.

144, 1275 (1907). 21. Robinson and Bogert, J . Ovg. , 1, 65 (1936). 22. Simon and Manguin, Compt. , 144, 1276 (1907). 23. German Pat. , 19, 817 (1934);Chern. Abstracts, 27, 1362 (1933). 24. Campbell and Schaffner, J . Am. Ckem. ,67, 86 (1945). 25. U. S . Pat. 2,451,610; Chetn. ADslracfs, 43, 1443 (1948). 26. Wiley, New York, 1950,p. 260. 27. Johnson, in Organic Reactions. Vol. 11, Wiley, New York, 1944, p. 177. 28. Johnson, in Organic Reactions. Vol. 11, p. 116. -79. , 56, 1853 (1923). 30. Johnson, in Organic Reactions.

Only two ring closure reactions are known ; most derivatives reported are prepared by procedures (b) and (c). In many instances derivatives made by procedure (c) have not been oriented. Phomazarin, a natural product, appears to be a highly substituted I-azaanthraquinone. ( a ) By Ring Closure. Application of the benzoylbenzoic acid type of synthesis, with quinolinic anhydride (XCVIII) replacing Chapter I 44 phthalic anhydride, gives a very small yield of 1 -azaanthraquinone (IV), which is very difficult to isolate and purify.

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