Chemistry of Heterocyclic Compounds: Condensed Pyridazines by Raymond N. Castle

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By Raymond N. Castle

Content material:
Chapter I Cinnolines (pages 1–321): Gary M. Singerman
Chapter II Phthalazines (pages 323–760): Natu R. Patel
Chapter III Azolo? and Azinopyridazines and a few Oxa and Thia Analogs (pages 761–1056): M. Tisler and B. Stanovnik

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Additional resources for Chemistry of Heterocyclic Compounds: Condensed Pyridazines Including Cinnolines and Phthalazines, Volume 27

Example text

The benzoic acid could only Cinnolines 32 have been derived from the 3-phenyl group and the 3-carbon atom of the cinnoline nucleus (31). Because the cinnoline ring system is so easily oxidized, at least by potassium permanganate or alkaline potassium ferricyanide, it is not feasible to prepare cinnoline-4-carboxylic acid (56) from 4-methylcinnoline (17) by direct oxidation. In fact, oxidation of 4-methylcinnoline with aqueous potassium permanganate at 28" C produces only a small amount of a material which does not precipitate when its alkaline solution is acidified.

In fact, quaternization of 4-methylcinnoline with simple alkyl halides occurs principally at N-2, and the cinnoline ethiodide which condensed with p-dimethylaminobenzaldehyde was almost certainly the 2-ethiodide. In general, alkylation of the alkyl- and arylcinnolines with alkyl halides or sulfates, such as dimethyl sulfate, occurs predominantly at 36 Cinnolines N-2 unless the steric effect of a group in the 3-position of the cinnoline ring shifts more of the alkylation to the N-1 position. For example, when 4methylcinnoline is quaternized with methyl iodide, the ratio of the N-2 to N-1 methyl salts obtained is l O : l , but 3-phenylcinnoline yields 78% of the N-1 salt and 22% of the N-2 salt with methyl iodide (29).

Phenylglyoxal Monophenylhydrazones Cyclization of the o-hydroxyphenylglyoxal monophenylhydrazones (25, B = hydrogen, methyl, or chlorine) to the corresponding 6-substituted 4-(o-hydroxyphenyl)cinnolines (26) has been effected by the action of fused aluminum chloride at 180-190" C for 5 min in the absence of a solvent. Cyclization could not be effected in the presence of inert solvents. Anhydrous zinc chloride, polyphosphoric acid, phosphorus oxychloride, and boron trifluoride did not cause cyclization to the cinnoline (11).

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