1,3,5-Triäthyl- und 1,3,5-Triphenylborazinderivate

Zusammenfassung Einige neue N-Triäthyl- bzw. N-Triphenylborazinderivate wurden hergestellt und ihre IR-Spektren mit denen bereits bekannter Verbindungen verglichen. Die Frequenzabhängigkeit der B—N-Hauptbande infolge der Art der Substitution an den B-Atomen wird diskutiert.

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Several new N-triethyl- and N-triphenylborazines have been prepared. IR-Spectra are recorded and compared with those of compounds already described. The frequency dependence of the B—N main band upon B-substitution is discussed.

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Herrn Prof. Dr. Dr. h. c.F.Wessely zum 70. Geburtstag gewidmet.     

Azo-1,3,5-triazines

The synthesis of variously substituted bis-triazinylhydrazines and their subsequent oxidation preferably with chlorine in a two-phase system to azo-1,3,5-triazines starting from cyanuric chloride is reported. Reaction of ethoxycarbonylhydrazine with cyanuric chloride followed by oxidation gave access to mono- and bis-ethoxycarbonyl-1,3,5-triazines, respectively. Azo-1,3,5-triazines proved to be very reactive dienophiles.     

Efficient solid-phase synthesis of 1,3,5-trisubstituted 1,3,5-triazine-2,4,6-triones

The solid-phase synthesis of 1,3-disubstituted and 1,3,5-trisubstituted 1,3,5-triazine-2,4,6-triones from MBHA and Wang resin is described. Reaction of resin-bound amino acids with isocyanates yield resin-bound ureas, which further react with chlorocarbonyl isocyanate in toluene at 65 degrees C to selectively afford the resin-bound 1,3-disubstituted 1,3,5-triazine-2,4,6-triones. Selective alkylation at the N-5 position of the resin-bound 1,3-disubstituted 1,3,5-triazine-2,4,6-triones was accomplished by treatment with alkyl halides in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The desired products were cleaved from their solid support and obtained in good yield and purity. The method can be employed in production of toltrazuril analogue libraries for identification of new anticoccidial agents.     

Heterocycles from heterocycles. - III[1]. 1,3,5-trisubstituted hexahydro-1,3,5-triazines-2-ones from 1,3,5-trisubstituted hexahydro-1,3,5-triazines and organic isocyanates

1,3,5-Triscubstituted hexahydro-1,3,5-trazin-2-ones 3 are easily obtained by the reaction of 1,3,5-trisub-stituted hexahydro-1,3,5-triazines 1 with organic isocyanates 2 . The reaction is believed to occur by the sequential addition to 2 of two molecules of the monomeric N-methyleneamines in thermal equilibrium with 1. Substituent scrambling at the operating temperature (120°) was negligible. The crystal structure of 1,3,5-triphenylhexahydro-1,3,5-triazin-2-one (3a) has been determined by X-ray diffraction methods.     

1,3,5-三乙酰基六氢均三嗪的小分子法合成反应机理研究

1,3,5-三乙酰基六氢均三嗪(1,3,5-triacetyl-1,3,5-triazacyclohexane,TRAT)是高性能单质炸药黑索金的关键硝化前体.本研究以小分子三聚甲醛和乙腈为原料,浓硫酸为催化剂,合成了TRAT,产率为89%.合成并表征了N,N'-亚甲基二乙酰胺和未见报道的三乙酰基二亚甲基三胺.根据已得到的几个中间体,推测了TRAT合成反应的可能机理.