- Reactions of Guanidine and Urea with Aminonitriles
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The aminonitriles 3a-f react with guanidine in DMF to yield the 5,5- resp. 5-substituted imidazolidine-2,4-diimines 2a-d resp. 2f, whereas 2e could not be isolated. 7,14-diazadispiro-pentadecan-15-on (7), 4-imino-1,3-diazaspirodecan-2-one (8a) and the 2,4-diaminotriazine (9) were isolated as byproducts. 1-Aminocyclohexancarbonitrile (3a) reacts with urea to the 4-imino-1,3-diazaspirodecan-2-one (8a); 8a can be prepared from (1-cyancyclohexyl)urea (11a) as well.The structures of the new compounds are proved by NMR-, IR- and mass spectra and the mechanism of the reaction is discussed. - Keywords: Aminonitriles, reaction with guanidine resp. urea; 1,3-Diazaspirodecan-2-one, 4-imino; 1,3-Diazaspirononan-resp. decan-2,4-diimimne; Guanidine, reactions with aminonitriles; Imidazolidin-2,4-diimines, 5-substituted; Urea, reactions with aminonitriles
- Wendelin, Winfried,Kern, Wolfgang,Zmoelnig, Ilse,Schramm, Hans-Wolfgang
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- Remediation of s-triazines contaminated water in a laboratory scale apparatus using zero-valent iron powder
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Atrazine, propazine and simazine were tested separately and in mixture by batch procedure in a laboratory-constructed apparatus. 3.751 of a buffered s-triazines pesticide solution was treated at room temperature by 325-mesh zero-valent iron powder (ZVIP) (20 g/l). High performance liquid chromatography was used to separate by-products and study the decline in the pesticide's concentrations. Results obtained show that the order of degradation was simazine, atrazine and then propazine. The half-lives (t(1/2)) of the s-triazines pesticides are, respectively, 7.4, 9.0 and 10.6 min when they are treated separately, and 9.8, 11.2 and 13.7 min when they are treated together under the same conditions. The final by-product obtained after 50 min of contact of simazine with ZVIP shows a shift to longer wavelength in its UV spectrum. A similar phenomenon is shown for atrazine and propazine. Identical primary by-products are produced and subsequently degraded to 4,6-(diamino)-s-triazine, which seems to be the major by-product of the reductive treatment process. Pathways for the degradation of the studied s-triazines by ZVIP are proposed. (C) 2000 Elsevier Science Ltd.
- Ghauch, Antoine,Suptil, Joel
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- Tri-s-TRIAZINE: SYNTHESIS, CHEMICAL BEHAVIOR, AND SPECTROSCOPIC AND THEORETICAL PROBES OF VALENCE ORBITAL STRUCTURE.
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The synthesis, physical properties, and chemical properties of unsubstituted tri-s-triazine (1,3,4,6,7,9,9b-hepta-azaphenalene) are reported. 2,4-diamino-1,3,5-triazine was treated with methyl N-cyanomethanimidate and NaOMe in Me//2SO/MeOH to give 2,4-bis(N prime -cyano-N-formamidino)-1,3,5-triazine, which was subjected to short vacuum pyrolysis to give tri-s-triazine. The compound gave no evidence of (a) formation of pi complexes with either electron-donor or electron-acceptor organic partners, (b) protonation, (c) alkylation, or (d) N-oxidation, yet it formed complexes with silver salts and decomposed in water. Photoelectron spectroscopic studies of tri-s-triazine have provided ionization potentials associated with the six highest occupied pi and six highest occupied lone-pair orbitals.
- Shahbaz,Urano,LeBreton,Rossman,Hosmane,Leonard
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- Metal free [4+1] and [5+1] annulation reactions to prepare heterocycles using DMF and its derivatives as one-carbon source
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1,2,4-Triazolo[3,4-a]pyridines and related heterocycles and substituted triazines were commonly discovered scaffolds in a variety of pharmaceutical and agrochemical agents. Herein, we report a highly efficient and practical method using DMF and its derivative for the [4+1] and [5+1] annulation reactions to prepare these heterocycles. This metal free reaction takes advantages of shelf stable DMF as solvent and carbon donor, imidazole chloride as a catalyst, the mild reaction condition tolerates a broad substrate range and substitutes. The prepared 3-unsubstituted 1,2,4-triazolo[3,4-a]pyridine and derivatives allow further introduction of a variety of functional group1 at 3-position.
- Liu, Lingfeng,Qiao, Chunhua,Shen, Bei,Xu, Yiwen
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- Colorant compositions and processes
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A process for making solid colored particles by preparing a reaction solution in water comprising formaldehyde, urea, a cyclic polyamine functional triazine compound, and acid. A dye can be incorporated into the reaction solution if a color other than white is desired. Particles are formed having an average particle size between 1 and 70 microns without the need to resort to crushing to break up agglomerates. Particles made by this process provide excellent color and are easily washable from a substrate when incorporated into a washable formulation. Additionally, it has been found that the incorporation of colored microcapsules of average size of 1-70 microns where the color is located primarily on or in the shell of the microcapsule also provides excellent washable compositions when incorporated into a washable formulation.
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- The Reactions of Guanidine and Urea with Cyanohydrines
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Action of guanidine or urea on cyclohexanone-, cyclopentanone-, cycloheptanone- and acetonecyanohydrine 3a-3d generates very different products: 3a reacts with guanidine in DMF to yield 1,3-diazaspirodecane-2,4-diimine (5a).Heating the components without solvent affords 7,14-diazadispiropentadecan-15-one (7), the guanidine not participating in the reaction; similarly 3b is transformed by guanidine to a pentacyclic dispirocompound (possible formulae 19 and 20), whereas 3d reacts to give 3,3,5,5-tetramethylpiperazine-2,6-dion (21).In 3-pentanone guanidine- cyanide condensates itself to give 2,4-diamino-triazine (22).Action of urea on 3a-3d yields the 4-imino-1,3-diazaspiroalkan-2-ones 6a-6c and the 4-imino-5,5-dimethylimidazolidin-2-one 6d resp.If the reaction of urea and 3d is carried out in DMF, however, 5,5-dimethyl-4-ureido-3-imidazolin-2-one (28) (or the tautomeric carbamoyliminoimidazolidinone 27) is produced.The structures of the compounds prepared are proved by NMR-, IR- and mass spectra. - Keywords: 1.3-Diazaspiroalkan-2-ones. 4-imino; 1.3-Diazaspirodecan-2.4-diimine; Guanidine-cyanide. reactions with ketones; Guanidine. reactions with cyanohydrines; 2-Imidazolines, 4-imino-5.5-disubstituted; Urea. reactions with cyanohydrines
- Wendelin, Winfried,Schramm, Hans-Wolfgang,Zmoelnig, Ilse
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p. 853 - 866
(2007/10/02)
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- Diuretics on the basis of N substituted 2,4 diamino s triazines by cyclisation of biguanides
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The structural class of 2,4 diamino s triazines (5) functioning as diuretics has become accessible by a novel preparatory procedure. The new synthesis is based on the aminomethinylating principle of s triazine (1), under the action of which biguanides (2) are cyclized to 5 passing through the intermediary states 3 and 4.
- Kreutzberger
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p. 1860 - 1862
(2007/10/04)
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