1911 Encyclopædia Britannica/Triazines

TRIAZINES, in organic chemistry, a series of cyclic corn pounds, containing a ring system composed of three carbon and three nitrogen atoms. Three series are possible, the positions of

CONTINENTAL TRIAS. MARINE TRIAS or THE ALPINE AND INDIAN TYPES. G . . . . . . Alpine Zone . .

erman Trias. England. North Alpine Region. bouth Alpine Region. Fossils India. America. Rhaetic or Ma alodgn

S a n d Stones PQ na rt h .gg Kossen Rhaetic Kossen limestone 2 and Clays beds 'C U -9 beds Dashstem beds and “ Hoch- Star Peak ES with /lvicula White Lias, E75 'Q Lithoden- Kalk and (Azzarola 14111614111 gcbergskalk " beds 2 contorta black pa- < Q EE dron Kalk Dolomite beds) 6011¢07'l¢l in part LZ per-shales, E =.

fl'13flS *ii 3 Aulacothyris Sandstones

Bone bed B one b eCL Q g limestone with dino-Swbensand- Red a “d £3 #ii fi S“§§§§ "” .?;1$1d2§ d§ {.l 5 Q stein mottls d *cg t' 7;=' ¢ Dachstein § g Dachstein a = marls Wlth 17,3 Q Q Kalk and -5 -5 Kalk and Turbo Coral mme- ., , § Q 'Oak ' salt QD '5 Coral 'U 'U Coral (Worthrnia) St(-me .Q Q. an § YP' ~' UV 'DZ limestones E E limestones solilarius 5-5'Schilfsand- Sum, §§ “*~§ -E g;= Halmles 3 »

Stein Varliousléf EE Q ~[-° »<. z beds Q

- . ... cooure ei-mf. — T' “ ""' Ois G, -em d0|Om Sandstoneg E5 an . 3. Opponitz Raibl beds Tmmtes Hauerztes D Taylorvillc Q- ite and marls gg' 11' hmestonff and Subbullalus beds E b@<1S°fC=-3 Lettenkohlen- (with“W{=§ - 3 EE -E d910m1t@ ' S it; forma = Sarlflsteill f@f's'f0nes) “5 is O 'cg Remgrabner cn Trachyreras d lp - »-Dplomitic Conglomer- /3,75 S. U Lbeds andi 'B 3: gg aomdes 0 omite Q iz§ ;..:““ = -2 “';;, f;“' »: webs Dfwm Sandstone. an mar S °'~'3 so -ll- .ti, Q SIQE il- beds with plants, -EE Ea 5 EE .Q 3 3" 'U C - Richmond,

M h 1-'»-.E R -5 2 63 G E;!'§ : gin Trachyoeras Daonella Virginia Haupt- LISC C - ' "“ E Cl mg 'U in ij: O G3 U0 gon beds balk is is -'§ limestone E Q § S E gas Weflgefl Daonella -D-°=-'E-* — and Part- Q: oi '° O 53 beds lommeli E nach beds $.13 Bl1Cl'i€¥1' P7,0t7ac]?yCc Anhydrite group, Di H 'V H as stem ras reitzi g dolomite and 3 § 3 lg beds

Ts marls with rock- °2 W: " "“"" "' "f' "" . —é salt and gypsum E gg; T) & li Tfmodosss beds Cgmmgs Ptychites Koipato beds -f-1 E 8 5' Q (Prezzo lime' trinodosus beds 3 < Mg jg “ Alpine cj, Z 3 stollel ...

§ Zellendolomit ET? U; 2: lVlkui<f{hel~ , EE (? 1;1 ;l§ 0 l3§ d Q . A <2 .2 ' fi H O U o 1 -:M

53 56 I; (part) SQ la; llsecoaro Q E Rhynchonella Wellenkalk and »-iw ='- Q dl mlestofle, o decussala Niti l1me-dolomite 2 5 8 < Glltlien' of -'ig Vlrglona ° ci Stone gg 'Es stein beds D5 § gg A limestone QE" iQ “ O "" Q 3 in

<L> U A O (, K5

Q2 ';Ef f Hezlenstro- gn Meekocems l"" I ~ .

Upper; division Uppermot- E; 3 Campil beds Campil beds Naiifm "ma beds § beds' Idaho or Roth glidlsand- E, , coslota prinolobm if "1 v . . . "

Middle division Pebble beds .Q, =§ sets beds sets beds p, ,, ,, ,;, ,, ,, ,, ,, ,, - beds £ 3 Of Haugtsznd' J, ” Q HL', , nd clarai 0, ,, Ce, ,, , = stem an os- - o

ag gesensandstein) ';, '§ gg? (Pet;§ g;n> Lower division Lower mot- 5 -F I U7 »§ 2

sandstones with tled sand- Q § " 'Q

4 Q

occasional oolite stone: III 3

(Rogenstein) ~ ~ D

the various units of the ring system being illustrated in the annexed formulae:—

C C C

N me cmc NI N

C N N / N C/C

N N N

α-Triazines, β-Triazines, Cyanidines.

Few simple derivatives of the α-series are known, those which have been prepared result by such reactions as the condensation of aminoguanidine or a similar type of compound (e.g. semicarbazide) with ortho-dike tones (J. Thiele, Ann., 1898, 302, p. 299):

NH-NH2 OC'CeH5 Nl'l'N

l-lN:C 'i' l -2 HN=C /C'CsHs§

NH2 5 C -CGH5

Wolff has obtained a chloro-derivative by the action of potassium cyanide on diazoacetophenone and subsequent treatment with acid. The phen-a-triazines are more numerous, and are obtained either by the action of concentrated acids on the formazyl compounds (E. Bamberger, Bef., 1893, 26, p. 2786):- C5H5N:N~ NrN

v/C-COCGHB s C@Hf, NH2--CSH4 I

C5H5'NH'lN N-C'COC6H5;

by the reduction of symmetrical acyl-ortho-nitrophenyl hydra zines (e.g. N02-CGH4-NH-NH~CHO); or in the form of dihydro derivatives by the condensation of aldehyde's with ortho-aminoazo compounds (H. Goldschmidt and Y. Rosell, Bef., 1890, 23, p. 487), or from the aminoazo compound and a mustard oil, the resulting thiocarbanilido derivative being heated with acetic acid (M. Busch, Bef., 1899, 32, p. 2960) 1/N-C(SH)'N-CsHs /N-C'NCsHs

C;H/ ' scH/ ' +Hs.,

°N-NH~c.H. 7 6N-N-C7H7 2

C. Harries (Ben, 1895, 28, p. 1223) has also shown that as-phenylhydrazino-acetic esters, when heated with form amide and substituted form amides under pressure, yield dihydrotriazinesicqi R CO-NR'-CH

CH, .N(C5H5)NH2+R “WHO 9 cH.~N<c.H.>-N ', The phen-a-triazines are yellow-coloured crystalline compounds of a somewhat basic character.

Derivatives of B-triazines are formed by the action of nitrous acid on ortho-aminobenzylamines (M. Busch, B87'.', 1892, 25, p. 445), or in small quantity by the action of nitrous acid on ortho-aminobenzoylphenylhydrazines (A. Konig and A. Reissert, Bcr.. 1899, 32, p. 782), the chief product in this latter reaction being an isoindazolone:

/CHg-Nl'lC¢;l'{;, Clrlg-NH~C6l'l.; /CH2~NC¢;l'l5 Celi4 9 CsHi 9CeH4 i-NH;-HCl

N:NCl NZN

The best drawn series of the triazines cyanidine series, members of which result of acid anhydrides with aromatic amidines 25' P' 1624): NH N c c H

A ' ' 6 5

2c.H, -c< +(CH3CO)2O 9 c.H.~c< >N; NH2 N IC-CH3

or by the condensation of aromatic nitriles with acid chlorides in the presence of aluminium chloride (Eitner and Krafft, Bef., 1892, 25, p. 2263). In using benzoyl chloride in this reaction the condensation is found to proceed better if a little ammonium chloride be added:

is the symmetrical or

from the condensation

(A. Pmner, Ber., 1892,

Cf, H, »C-Cl OC-C@H5

2C¢H. +C5Hu $ Q/

N -C(C¢H5):N

The cyanidines behaveas weak bases. Mention may be made here of cyanuric acid, H3C3N3O3, which ring system as the cyanidines. It was first prepared by C. Scheele and is formed when urea is strongly heated or when cyanuric chloride is treated with water. It is usually represented by the inset formula and is closely related to cyanic acid and c yam elide, the relationships existing between the three compounds being shown in the diagram (see also A. Hantzsch, Ber., 1906, 39, p. 139): Contains the same

N-c-OH

HOC/ N

N:(T4OH

Ordinary

temperature / Cyamelid Decomposes easily (CNOH)3

Cyanic acid/ CO NH

CNOH HO ions Z 2+~ =

l/ /, /

High temperature ; Cyanuric acid; Decomposes with difficulty.