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QUINAZOLINES (Phenmiazines or benzopy...

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Originally appearing in Volume V22, Page 753 of the 1911 Encyclopedia Britannica.
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QUINAZOLINES (Phenmiazines or benzopyrimidines) , in organic See also:chemistry, heterocyclic compounds of the structure shown in the inset See also:formula. They may be regarded as resulting (\)~ from the See also:fusion of a See also:benzene with a pyrimidine \N(3) See also:nucleus in the 5.6 position. They are isomeric I~I aminobenzaldehydes and ortho-aminoketones (A. Bischler, Ber., /CHO /CH:N 1891—95) : See also:C6H4( +NH3 = C6H4C I + 2 See also:H2O; NH.CO.R N : CR and from the corresponding dihydro compounds on oxidation with See also:potassium permanganate. They are See also:stable, See also:tertiary bases, and may be distilled without decomposition; they See also:form addition products with alkyl iodides and See also:double salts with mercuric and See also:platinum chlorides. On reduction with See also:sodium in presence of See also:alcohol they yield dihydro derivatives. Those in which the :CH See also:group adjacent to the benzene nucleus is unsubstituted are oxidized by chromic See also:acid to ketodihydroquinazolines (quinazolones). Quinazoline (C6H2N,) is obtained by oxidizing its dihydro-derivative with potassium ferricyanide. The dihydro derivatives exist in three different See also:series, since the addition of two atoms of See also:hydrogen in the diazine See also:ring can take See also:place in three different positions, namely, in the 3.4, 1.4 and 1.2 positions, and these different types are distinguished by the symbols Al, See also:A2, A3, denoting that the double linkage is between the first and second, second and third, and third and See also:fourth atoms in the diazine ring. The Al series, which are obtained by the elimination of the elements of See also:water from the acidyl derivatives of ortho-aminobenzylamines, are rather strong bases which form stable salts and yield the corresponding keto derivatives on oxidation (C. Paal, Ber., 1889-1896). 4-Keto-dihydroquinazoline (/3-quinazolone) is formed by oxidizing the dihydro See also:base with potassium permanganate; by boiling acidyl-ortho-aminobenzamide with water (A.

Weddige, Jour. prak. Chem., 1885, (2) 31, p. 124) ; or by See also:

heating See also:ant hranilic acid with formamide (S. Niementowski, Ber., 1895, 28, p. 443). It reacts both in the enol and keto forms, yielding both N-See also:ethers and 0-ethers, the latter being obtained by the See also:action of sodium alcoholates on 4-chlorquinazolines. The A2 series is obtained by heating acidyl-ortho.. aminobeuzylamines with See also:zinc chloride, whilst the A3 series, which !!~ N (1) holic See also:ammonia on the acidyl derivatives of orthowith the cinnolines, See also:phthalazines and quinoxa-(2) lines. They maybe obtained by the action of alco- is only known in the form of its keto derivatives (a-quinazolines), results from the fusion of See also:urea with ortho-aminobenzaldehydes and benzophenones, the elements of water and of ammonia being eliminated (S. See also:Gabriel and Th. Posner, Ber., 1895, 28, p. 1037). They possess feeble basic and phenolic characters.

The tetra-hydroquinazolines are obtained by reducing the quinazolines and dihydroquinazolines and by condensing ortho-aminobenzylamine with See also:

aldehydes (M. See also:Busch, Jour. prak. Chem., 1896, (2) 53, p. 414). The ring is easily split on See also:hydrolysis, giving rise to ortho-disubstituted benzenes. The keto derivatives of this series result by the action of carbonyl chloride on ortho-aminobenzylamines of the type H_N.See also:C6H,.CH,NHR (M. Busch, Ber., 1892, 25, p. 2853), or from the urea derivatives of ortho-aminobenzylamine. They are weak bases which are indifferent to both acids and alkalis, and which on oxidation yield the corresponding 2.4-diketo derivatives.

End of Article: QUINAZOLINES (Phenmiazines or benzopyrimidines)

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