Cyanuric Chloride Derivatives. III. Alkoxy-s-triazines

Dudley, James R.; Thurston, Jack T.; Schaefer, Frederic C.; Holm-Hansen, Dagfrid; Hull, Clarence J.; Adams, P.T.

doi:10.1021/ja01151a003

Cited by 158 publications

(69 citation statements)

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“…2,4-Dichloro-6-methoxy-1,3,5-triazine was prepared by modification of reported procedure. 39) Other chemicals and solvents were obtained from commercial sources and used without further purification. IR spectra were measured on a Nicolet FT-IR AVATAR 360 spectrometer.…”

Section: Methodsmentioning

confidence: 99%

Immobilized Triazine-Type Dehydrocondensing Reagents for Carboxamide Formation: ROMP-Trz-Cl and ROMP(OH)-Trz-Cl

et al. 2007

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The advance in combinatorial chemistry has resulted in the development of solid-supported reagents that can be applied to automated synthesis of a target molecule. As a result, many useful reagents that are well established in the field of solution-phase chemistry have been applied to immobilized reagents. [1][2][3][4][5][6][7][8][9] There have been some recent reports on the preparation of immobilized reagents for dehydrocondensation.10-18) However, since most of these reagents are immobilized by connecting dehydrocondensing reagents to insoluble carriers such as polystyrene and silica gel, they would be prepared by inefficient chemical transformation on the insoluble carrier under heterogeneous conditions. In addition, the weight proportion of the solid carrier relative to the amount of solidsupported reagent is generally high, which inevitably results in the generation of large amounts of waste; this is a serious problem common to solid-supported reagents. To resolve this issue, we developed a new immobilized triazine-type dehydrocondensing reagent by polymerizing the dehydrocondensing reagent itself.19) This polymer reagent is based on the condensing agent, 4,6-dimethoxy-1,3,5-triazinyl-2-methylmorpholinium chloride (DMT-MM) [20][21][22][23][24][25][26] and is a crosslinked polymer prepared by co-polymerizing tetra(ethylene glycol) bis(4-chloro-6-methoxy-1,3,5-triazin-2-yl) ether and tris(2-aminoethyl)amine, which is easily substituted onto the triazine ring under weakly basic conditions.In this work, we developed another application for polymer-type triazine condensing reagents: immobilization by well-established ROMP (ring opening metathesis polymerization) method, in which the reaction proceeds rapidly and with high yield under mild neutral conditions. The dramatically expanded ROMP methodology, based on the work of Grubbs et al. in the 1990s, has been developed as an effective method for acquiring high-loading polymer reagents by polymerizing the reagent unit as a monomer.27-31) Barrett et al. actively developed ROMP-gel supported reagents using this methodology, and reported many excellent immobilized reagents. 4,9,[32][33][34] These reagents have several advantages in addition to high-loading, e.g., high tolerance of the methathesis catalysts for diverse functionalities, and readily available monomers from inexpensive precursors. Recently, ROMP supported coupling reagents carrying fluoroformamidinium or 2-bromopyridinium were also reported.11) In this case, however, preparation of the monomers, which requires operation of 3-4 steps, seems not to be very easy.Our monomer 1a was readily prepared by reacting cyanuric chloride consecutively with 5-norbornene-2-methanol and MeOH (Chart 1). A CH 2 Cl 2 solution of the resulting monomer and cross-linker 2 35) in a mixing ratio of p : q, as shown in Table 1, was allowed to react in the presence of 0.1 mol% Grubbs' catalyst 3 to produce four kinds of polymer with cross-linking percentages of 10, 30, 50 and 100%. The polymer reagents exhibited condensation activ...

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Section: Methodsmentioning

confidence: 99%

Immobilized Triazine-Type Dehydrocondensing Reagents for Carboxamide Formation: ROMP-Trz-Cl and ROMP(OH)-Trz-Cl

et al. 2007

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“…All diaminochloro-s-triazines were prepared as previously described by Thurston et al (25). Alkoxy-s-triazines were prepared from the alcohols and sodium bicarbonate as previously described by Dudley et al (4). 2-Methylthio-4,6-diamino-1,3,5-triazine [(Ms)AAT] was prepared by heating 2-chloro-4,6-diamino-1,3,5-triazine with equimolar amounts of sodium hydrosulfite and methylmercaptan disulfide at 90°C in water.…”

Section: Methodsmentioning

confidence: 99%

“…Ametryn sulfoxide was synthesized by adding, slowly over 30 min, 1.5 equivalents of m-chloroperoxybenzoic acid to ametryn in chloroform under nitrogen at 5°C. After an additional 30 min, the reaction mixture was washed twice with saturated NaHCO 3 , dried over MgSO 4 , and filtered through silica gel. Contaminants of ametryn and a small amount of the sulfone were removed by repeated chromatography on silica gel with dichloromethane as a solvent and slow crystallization of the product from dichloromethane.…”

Section: Methodsmentioning

confidence: 99%

Substrate Specificity and Colorimetric Assay for Recombinant TrzN Derived from Arthrobacter aurescens TC1

Shapir

Rosendahl

Johnson

et al. 2005

Appl Environ Microbiol

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The TrzN protein, which is involved in s-triazine herbicide catabolism by Arthrobacter aurescens TC1, was cloned and expressed in Escherichia coli as a His-tagged protein. The recombinant protein was purified via nickel column chromatography. The purified TrzN protein was tested with 31 s-triazine and pyrimidine ring compounds; 22 of the tested compounds were substrates. TrzN showed high activity with sulfur-substituted s-triazines and the highest activity with ametryn sulfoxide. Hydrolysis of ametryn sulfoxide by TrzN, both in vitro and in vivo, yielded a product(s) that reacted with 7-chloro-4-nitrobenz-2-oxa-1,3-diazole (NBD-Cl) to generate a diagnostic blue product. Atrazine chlorohydrolase, AtzA, did not hydrolyze ametryn sulfoxide, and no color was formed by amending those enzyme incubations with NBD-Cl. TrzN and AtzA could also be distinguished by reaction with ametryn. TrzN, but not AtzA, hydrolyzed ametryn to methylmercaptan. Methylmercaptan reacted with NBD-Cl to produce a diagnostic yellow product having an absorption maximum at 420 nm. The yellow color with ametryn was shown to selectively demonstrate the presence of TrzN, but not AtzA or other enzymes, in whole microbial cells. The present study was the first to purify an active TrzN protein in recombinant form and develop a colorimetric test for determining TrzN activity, and it significantly extends the known substrate range for TrzN.

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“…Another is a popular procedure that was first reported by Dudley and his colleagues. 10 In the procedure, a mixture of acetone and water (1:1, v/v) is used as solvent and aq. NaOH is used as acid acceptor.…”

Section: Syntheses and Characterization Of Taptmentioning

confidence: 99%

Synthesis and characterization of triallylphenoxytriazine and the properties of its copolymer with bismaleimide

Fang

Jiang

2001

J of Applied Polymer Sci

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ABSTRACT:A new modifier for bismaleimide (BMI), 2,4,6-tris(2-allylphenoxy)-1,3,5-triazine (TAPT), with higher yield was prepared by a phase-transfer catalyzing (PTC) procedure through the reaction of cyanuric chloride with 2-allylphenol in the presence of aq. NaOH using tetrabutyl ammonium bromide in chloroform. The thermo-homopolymerization behavior of TAPT was investigated by differential scanning calorimetry (DSC), and the results showed that TAPT does not polymerize on heating. The copolymerization reaction of TAPT and 4,4'-(bismaleimidophenyl) methane (BMDPM) was also studied. and the results showed that TAPT can effectively improve mechanical properties of BMDPM. The better results were obtained when the TAPT composition was in the range 30 -40 wt %. The glass fabric reinforced TAPT/BMDPM matrix composite with excellent mechanical and electric properties could be prepared by processing the resin (30 wt % TAPT) in dimethylformamide (DMF)/toluene (1:1, v/v) solution.

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Cyanuric Chloride Derivatives. III. Alkoxy-s-triazines

Cited by 158 publications

References 1 publication

Immobilized Triazine-Type Dehydrocondensing Reagents for Carboxamide Formation: ROMP-Trz-Cl and ROMP(OH)-Trz-Cl

Immobilized Triazine-Type Dehydrocondensing Reagents for Carboxamide Formation: ROMP-Trz-Cl and ROMP(OH)-Trz-Cl

Substrate Specificity and Colorimetric Assay for Recombinant TrzN Derived from Arthrobacter aurescens TC1

Synthesis and characterization of triallylphenoxytriazine and the properties of its copolymer with bismaleimide

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