In classifying closed chain compounds, the first step consists in dividing them into: (1) carbocyclic, in which the ring is composed solely of carbon atoms - these are also known as homocyclic or isocyclic on account of the identity of the members of the ring - and (2) heterocyclic, in which different elements go to make up the ring.
PYRIMIDINES, METADIAZINES or Miazines, in organic chemistry, a series of heterocyclic compounds containing a ring complex, composed of four carbon atoms and two nitrogen atoms, the nitrogen atoms being in the meta-position.
XANTHONE (dibenzo-y-pyrone, or diphenylene ketone oxide), C H 0 in organic chemistry, a heterocyclic compound containing the ring system shown below.
There also exists an extensive class of compounds termed the " heterocyclic series " - these compounds are derived from ring systems containing atoms other than carbon; this class is more generally allied to the aromatic series than to the aliphatic.
Carbocyclic rings will next be treated, benzene and its allies in some detail; and finally the heterocyclic nuclei.
And >- CH, the first characterizing the polymethylene and reduced heterocyclic compounds, the second true aromatic compounds.
The elements which go to form heterocyclic rings, in addition to carbon, are oxygen, sulphur, selenium and nitrogen.
Thus ortho-phenylene diamine yields the following products: N H N ./`N; Xn NZ In some cases oxidation of condensed benzenoid-heterocyclic nuclei results in the rupture of the heterocyclic ring with the formation of a benzene dicarboxylic acid; but if the aromatic nucleus be weakened by the introduction of an amino group, then it is the benzenoid nucleus which is destroyed and a dicarboxylic acid of the heterocyclic ring system obtained.
Heterocyclic rings may be systematically surveyed from two aspects: (I) by arranging the rings with similar hetero-atoms according to the increasing number of carbon atoms, the so-called " homologous series "; or (2) by first dividing the ring systems according to the number of members constituting the ring, and then classifying these groups according to the nature of the hetero-atoms, the so-called " isologous series."
As a useful preliminary it is convenient to divide heterocyclic ring systems into two leading groups: (I) systems resulting from simple internal dehydration (or similar condensations) of saturated aliphatic compounds - such compounds are: the internal anhydrides or cyclic ethers of the glycols and thioglycols (ethylene oxide, &c.); the cyclic alkyleneimides resulting from the splitting off of ammonia between the amino groups of diaminoparaffins (pyrrolidine, piperazine, &c.); the cyclic esters of oxycarboxylic acids (lactones, lactides); the internal anhydrides of aminocarboxylic acids (lactams, betaines); cyclic derivatives of dicarboxylic acids (anhydrides, imides, alkylen-esters, alkylenamides, &c.).
The skeletons of these types are (the carbon atoms are omitted for brevity): We have previously referred to the condensation of heterocyclic ring systems containing two vicinal carbon atoms with benzene, naphthalene and other nuclei.
The more important nuclei of this type have received special and non-systematic names; when this is not the case, such terms as phen-, benzo-, naphthoare prefixed to the name of the heterocyclic ring.
THIAZOLES, in organic chemistry, a series of heterocyclic compounds containing the grouping shown below; the replaceable hydrogen atoms in which are designated a, (3 and µ.
Pyrocatechin readily condenses to form heterocyclic compounds; cyclic esters are formed by phosphorus trichloride and oxychloride, carbonyl chloride, sulphuryl chloride, &c.; whilst ortho-phenylenediamine, o-aminophenol, and o-aminothiophenol give phenazine, phenoxazine and thiodiphenylamine.
ACRIDINE, C13H9N, in chemistry, a heterocyclic ring compound found in crude coal-tar anthracene.
TRIAZOLES (pyrro-a and (3'-diazoles), in organic chemistry, a series of heterocyclic compounds containing the ring complex (annexed formula).