Human organ alkaline phosphatases: discrimination by several means including starch gel electrophoresis of axtienzysie‐enzyme supernatant fluids*

The synthesis, properties, and application of condensing reagents derived from 1,3,5-triazines are described. The mechanism of activation of carboxylic function, structure of reactive intermediates, and mechanism of acylation of nucleophiles are presented. The synthetic versatility of mono- and bifunctional reagents for syntheses in solution, triazine-based immobilized reagents, chiral triazines for enantiodifferentiating syntheses, are discussed. The scope and limitation of the synthetic utility of triazine reagents in the preparation of heterocyclic compounds, amides, esters, oligopeptides-including large-scale syntheses and use in the combinatorial chemistry-is demonstrated.

Triazine-based condensing reagents

Use of chiral monohalo-s-triazine reagents for the liquid chromatographic resolution of dl-amino acids

Publisher Summary This chapter presents the reactivity pattern of azines with nucleophiles, mainly in the reactions of chloro derivatives with an anionic nucleophile (alkoxide) and with a neutral nucleophile (ammonia or aliphatic amine). The alternative mechanisms of nucleophilic substitution of aromatic compounds—namely, heteroaryne mechanism; SN1 mechanism; ring-opening and recyclization; and synchronous or one-stage bimolecular mechanism—are also described in the chapter. The cationization of the azine–nitrogen promotes nucleophilic substitution at all positions, because the electronegativity of the nitrogen is increased. This change increases the electron deficiency (ground state) and decreases the localization energy and resistance of the π electron system to interact in the transition state with nucleophiles. The reversible interaction of the carbonyl group with an azine lone-pair facilitates substitution adjacent to the heteroatom by the anion of a β-hydroxyethyl ketone. A similar cyclic intermediate is presumably responsible for the cyclization of acetylene dicarboxylic esters with azines.

Reactivity of Azine, Benzoazine, and Azinoazine Derivatives with Simple Nucleophiles

Mono- and bis-(2-hydroxyphenyl)-s-triazines 4, 14, 18, 22, 28, 29 can be prepared by (a) reaction of salicylic acid esters 2 with amidines 3; (b) reaction of 4H-1, 3-benzoxazin-4-ones 10 with amidines 3; and (c) Friedel-Crafts-reaction of chloro-s-triazines 26, 27 with resorcinol 24.



In case (b) the path of reaction is determined by the character of substituent R4 in 10. Scope and limitations of these reactions and accessibility of starting materials are discussed.

Die Synthese von asymmetrisch substituierten o‐Hydroxyphenyl‐s‐triazinen

An improved synthesis of 4,6-dichloro-2-phenoxy-1,3,5,-triazine from cyanuric chloride and phenol in the presence of collidine (2,4,6-trimethyl-pyridine) induced us to investigate the scope and limitation of the substitution of one chlorine atom in cyanuric chloride and the influence of the base used as an acid acceptor. Phenols, thiophenols, alcohols, thiols and oximes generally reacted with cyanuric chloride in the presence of collidine giving good yields of the corresponding substitution derivatives. The herbicidal and fungicidal properties of the compounds are dealt with and are briefly discussed. The influence of the alkyl or aryl side chain on the biological activity was determined. For this reason some derivatives mentioned in the literature were included for comparison in our biological tests.

Investigations on herbicides II: 2-Alkyloxy- and 2-aryloxy -4,6-dichloro-1,3,5-triazines 2-Alkylthio- and 2-arylthio-4,6-dichloro-1,3,5-triazines

In view of their herbicidal properties a number of similarly or differently 2,4-substituted 6-chloro-1,3,5-triazines was synthesized. Their herbicidal properties are briefly discussed.

Investigations on herbicides III: 2,4‐Disubstituted 6‐chloro‐1,3,5‐triazines

IN the course of investigations on s-triazines, we have discovered a new synthesis of 2-alkoxy- and 2-alkylthio-4,6-dichloro-s-triazines. These substances can be obtained by the reaction of an alcohol or a thiol with cyanuric chloride and 2,6 x collidine as the acid acceptor. The yield was approximately 80–90 per cent. In a further systematic investigation, we found that in these compounds the chlorine atom can be specifically substituted in good yield by an alkylamino, alkyloxy or alkylthio group.

New s -Triazine Herbicides

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Investigations on herbicides II: 2-Alkyloxy- and 2-aryloxy -4,6-dichloro-1,3,5-triazines 2-Alkylthio- and 2-arylthio-4,6-dichloro-1,3,5-triazines

Investigations on herbicides III: 2,4‐Disubstituted 6‐chloro‐1,3,5‐triazines

New s -Triazine Herbicides