ISBN-10: 0470186518

ISBN-13: 9780470186510

ISBN-10: 0470375213

ISBN-13: 9780470375211

Content material:
Chapter I Azanaphthacenes (pages 3–56): Eleanor R. Wabster
Chapter II Azabenz[a]Anthracenes (pages 57–132): Jean V. Crawford and Eleanor R. Wabster
Chapter III Azabenzo[c]Phenanthrenes (pages 133–149): Eleanor R. Wabster
Chapter IV Azachrysenes (pages 151–183): Jean V. Crawford
Chapter V Azatriphenylenes (pages 185–199): Jean V. Crawford
Chapter VI Azabenzanthrenes (pages 201–293): C. F. H. Allen, D. M. Burness and F. W. Spangler
Chapter VII Azapyrenes (pages 295–310): Eleanor R. Webster

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Additional resources for Chemistry of Heterocyclic Compounds: Six-Membered Heterocyclic Nitroggen Compounds With Four Condensed Rings, Volume 2

Sample text

S Diff. ; ycllow with green F1; yellow S green m. >360"; as in XXXIII + Dec. on heating; blue S m. >280°; ins. 0; blood-red S; sol. Ha; violet H without FI ; orangcred OH- without FI; blue S, with H i 0 red Very diff. sol. Pmprrtin I. Azanaphthacenes 54 XI. i N-Phenyl-2,3-dihydroxyquinoxaline(XLI I) and o-phenylenediamine give a poor yield of 5-phenyl-5,l ldihydro-5,6,11,12-tetrazanaphthacene (XLIII). The properties of these three derivatives show great simi- 011 II,N C6H5 C6H5 XLlll XLII larities to those of fluoflavin (XXXIII) itself, and the reported characteristics of the monochloro derivative (XL) indicate that it is probably identical with Hinsberg’sea chloro compound (XXXV).

I. 2695 1 ReissertJ6 first synthesized compounds of the 5,6-diazanaphthacene series as an extension of work with 1,8-naphthyridines,* and investigated a number of these tetracyclic compounds fairly extensively. He attempted the ring closure of di-o-nitrobenzylmalonic ester (XXI) with dilute hydrochloric acid in a sealed tube, but recovered the starting material unchanged. With more concentrated acid, the product obtained is di-(0-nitrobenzy1)acetic acid (XXII). Reduction of this dinitro acid or its ethyl ester is readily carried out with a variety of reducing agents, the best of which is zinc and hydrogen chloride; but the reaction gives not the expected diamino acid (XXIIIa), but a basic compound, CI#H14NZ,i.

9 H m. 181 ; very sol. 0 m. 309' 2 m. >350° rn m. 292'; ins. OH- cold, sol. blue hot mputhr Diazanapht hacenes 21 2. Diazanaphthacenes Examples of only six of the twenty-one possible diazanaphthacenes (in which the nitrogens arc not common to two rings) have been reported; in the case of the 1,ll-diaza isomer, the probability is great that an angular four-ring system was obtained rather than the linear. Although the 5,6- and 5,12-diaza compounds have been more fully investigated than any of the others, the information available on these examples is surprisingly limited, both in scope and completeness.

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Chemistry of Heterocyclic Compounds: Six-Membered Heterocyclic Nitroggen Compounds With Four Condensed Rings, Volume 2


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