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Encyclopedia Britannica



PHTHALAZINES (benzo-orthodiazines or benzopyridazines)

This article appears in Volume V21, Page 545 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: PER-PIG
PHTHALAZINES (benzo-orthodiazines or benzopyridazines) , in organic
chemistry
  a
group
  of heterocyclic compounds containing the
ring
  complex shown in
formula
  I. They are isomeric with the cinnolines (q.v.). The
parent
  substance of the
group
 , phthalazine, CBH6N2, is best obtained from the condensation of w-tetrabromorthoxylene with hydrazine (D. Gabriel, Ber., 1893, 26, p. 2210), or by the reduction of chlorphthalazine with
phosphorus
  and hydriodic acid (Ber., 1897, p. 3024). It possesses basic properties and forms addition products with alkyl iodides. On oxidation with alkaline potassium permanganate it yields pyridazine dicarboxylic acid.
Zinc
  and hydrochloric acid decompose it with formation of orthoxylylene diamine.
The keto-hydro derivative phthalazone, C8H6ON2, (
formula
  II.), is obtained by condensing hydrazine with orthophthalaldehydoacid. On treatment with
phosphorus
  oxychloride it yields a chlorphthalazine which with
zinc
  and hydrochloric acid gives isoindole, C8H,N, and with tin and hydrochloric acid phthalimidine, C8H2ON, the second nitrogen atom being eliminated as
ammonia
 .
\I NIN I \I CO NH
\/\/ N I\/\CH/N
I. Phthalazine. II. Phthalazone.


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