cas 2547-66-2, 1,3,5-TRIBENZYLHEXAHYDRO-1,3,5-TRIAZINE

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Hunt,Wagner
p. 1792,1798
(1951)
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Structural and Thermodynamics Studies on Polyaminophosphonate Ligands for Uranyl Decorporation
The development of actinide decorporation agents with high complexation affinity, high tissue specificity, and low biological toxicity is of vital importance for the sustained and healthy development of nuclear energy. After accidental actinide intake, sequestration by chelation therapy to reduce acute damage is considered as the most effective method. In this work, a series of bis- and tetra-phosphonated pyridine ligands have been designed, synthesized, and characterized for uranyl (UO22+) decorporation. Owing to the absorption of the ligand and the luminescence of the uranyl ion, UV-vis spectroscopy and time-resolved laser-induced fluorescence spectroscopy (TRLFS) were used to probe in situ complexation and structure variation of the complexes formed by the ligands with uranyl. Density functional theory (DFT) calculations and X-ray absorption fine structure (XAFS) spectroscopy on uranyl-ligand complexes revealed the coordination geometry around the uranyl center at pH 3 and 7.4. High affinity constants (log K ～17) toward the uranyl ion were determined by displacement titration. A preliminary in vitro chelation study proves that bis-phosphonated pyridine ligands can remove uranium from calmodulin (CaM) at a low dose and in the short term, which supports further uranyl decorporation applications of these ligands.
Ye, Gaoyang,Roques, Jérome,Solari, Pier-Lorenzo,Den Auwer, Christophe,Jeanson, Aurélie,Brandel, Jérémy,Charbonnière, Lo?c J.,Wu, Wangsuo,Simoni, éric
p. 2149 - 2159
(2021)
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McDonagh,A.F.,Smith,H.E.
p. 8 - 12
(1968)
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Synthesis of highly functional imidazole derivatives via assembly of 2-unsubstituted imidazole N-oxides with CH-acids and arylglyoxals
A novel and convenient method for the synthesis of a wide range of polyfunctional imidazole derivatives based on the three-component condensation of imidazole N-oxides with CH-acids and arylglyoxals has been developed. This reaction proceeds smoothly in moderate-to-good yields with a wide range of starting materials.
Perevalov, Valery P.,Mityanov, Vitaly S.,Lichitsky, Boris V.,Komogortsev, Andrey N.,Kuz'mina, Ludmila G.,Koldaeva, Tatyana Yu.,Miroshnikov, Vladimir S.,Kutasevich, Anton V.
(2020)
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Synthesis and Cytotoxic Activity of Hexahydro-1,3,5-triazine Derivatives through Ring Condensation
As a part of a research program for pharmacologically interacting sym-triazine derivatives with hexahydrotriazine ring, novel hexahydrotriazine derivatives (1?13) were successfully synthesized. The synthesis of hexahydrotriazines was carried out from the assembly of three molecules of various amines and three molecules of formaldehyde by “1 + 1 + 1 + 1 + 1 + 1” cycloaddition. The synthesis mechanism is probably passes through imines, which trimerizes to give the hexahydrotriazine ring. All synthesized hexahydrotriazines (1–13) were screened for their cytotoxic activity by cancer cells. As a result, compound 1–9 reduced the viability of T98G cells in a concentration-dependent manner. At a concentration of 100 μM, compound 9 exhibited the greatest cytotoxicity at 94.6%. The reason is that compound 9 is C5H5N that has a resonance hybrid structure and exhibits aromaticity. It is considered to be active because it has a structure that is a raw material for pyridine derivatives as mainly medicines and pesticides.
Bae, Song Mi,Kang, Sung Young,Song, Ju Hyun
p. 840 - 846
(2021)
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Synthesis of α-Amino Tertiary Alkylperoxides by Lewis Acid-Catalyzed Peroxidation of 1,3,5-Triazines
α-Substituted peroxides have been found in natural products and are widely used as anti-malarial agents. Zn(OTf)2-catalyzed peroxidation of 1,3,5-triazines has been developed, accessing diversely substituted α-amino tertiary alkylperoxides with high efficiency. Mechanistic investigations and useful synthetic application of the products have also been presented.
Liu, Lijuan,Shi, Zhichao,Zhang, Xun,Zhan, Feng,Lin, Jin-Shun,Jiang, Yuyang
supporting information
p. 3487 - 3491
(2021/09/20)

Facile Access to 3-Unsubstituted Tetrahydroisoquinolonic Acids via the Castagnoli-Cushman Reaction
Hitherto undescribed 3-unsubstituted tetrahydroisoquinolonic acids (isolated as their respective methyl esters) were accessed for the first time by the uncatalyzed, thermally promoted Castagnoli-Cushman reaction (CCR) of homophthalic anhydride (HPA) and a series of 1,3,5-triazinanes. The moderate yields observed in some cases are most likely associated with a persistent impurity also formed in these reactions. The new scaffold is expected to find novel medicinal utility (compared to the traditional CCR adducts) because it lacks a substituent at the 3-position.
Guranova, Natalia,Dar'In, Dmitry,Krasavin, Mikhail
p. 2001 - 2008
(2018/03/06)

Gold-Catalyzed Tandem Dual Heterocyclization of Enynones with 1,3,5-Triazines: Bicyclic Furan Synthesis and Mechanistic Insights
A general and unprecedented gold-catalyzed tandem dual heterocyclization reaction of enynones with 1,3,5-triazines has been developed, which provides bicyclic fused furans in high to excellent yields under mild reaction conditions. In addition, mechanistic studies indicate that the reaction goes through a stepwise [3+2+2]-cycloaddition of furanyl gold intermediate, which is generated from gold-catalyzed cyclization of enynone, with two molecules of formaldimines derived in situ from 1,3,5-triazine, instead of formal [4+3]-cycloaddition.
Zheng, Yang,Chi, Yongjian,Bao, Ming,Qiu, Lihua,Xu, Xinfang
p. 2129 - 2135
(2017/02/26)

A new and efficient procedure for the synthesis of hexahydropyrimidine-fused 1,4-naphthoquinones
A new and efficient method for the synthesis of hexahydropyrimidine-fused 1,4-naphthoquinones in one step with high yields from the reaction of lawsone with 1,3,5-triazinanes was developed.
Reis, Marcelo Isidoro P.,Campos, Vinícius R.,Resende, Jackson A. L. C.,Silva, Fernando C.,Ferreira, Vitor F.
supporting information
p. 1235 - 1240
(2015/08/18)

Diamino- and mixed amino-amido-N-heterocyclic carbenes based on triazine backbones
The synthesis of novel hexahydrotriazine-based NHCs from easily available starting materials is described. Tribenzyltriazacyclohexane 1 is converted stepwise to the six-membered diamino carbene 3 with a saturated ring structure. Analogously, the cyclic mixed amino-amido carbene 12 is obtained starting from a cyclic urea derivative. Both carbenes were characterized by trapping reactions with sulfur and selenium as well by the preparation of metal complexes of the type (COD)MX-NHC (M = Rh, Ir; COD = 1,5-cyclooctadiene), which were converted to the respective dicarbonyl complexes (CO)2MX-NHC. IR spectra of the carbonyl derivatives allowed the Tolman electronic parameter to be determined for carbenes 3 (2052 cm-1) and 12 (2058 cm-1) and revealed a shift of 6 cm-1 due to the presence of one amide function. X-ray structure determinations are reported for an amidinium species, a carbene sulfide, and the (COD)RhBr complex of the amino-amido carbene 12.
Makhloufi, Abdelaziz,Frank, Walter,Ganter, Christian
supporting information; experimental part
p. 2001 - 2008
(2012/04/23)

Method of synthesis of phosphinic acids based on hypophosphites: VIII.1 synthesis of α-aminoalkylphenethylphosphinic acids
Development of methodology of double Arbuzov rearrangement based on hypophosphites allows a one-pot formation of two unsymmetrical phosphorus-carbon bonds by the Michael-Pudovik type reaction of stepwise addition of the intermediately forming silyl esters of trivalent phosphorus to different unsaturated compounds. A procedure was developed of the synthesis of α-aminoalkylphenethylphosphinic acids. Bis-(trimethylsilyl) phenethylphosphonite formed as a result of the addition of bis(trimethylsilyl) hypophosphite to styrene in situ was added without isolation from the reaction mixture to Schiff bases obtained preliminary from benzylamine or diphenylmethylamine and various aldehydes. The subsequent removal of N-protecting groups by hydrogenation or acidic hydrolysis gave a number of new α-aminoalkylphenethylphosphinic acids.
Dmitriev,Ragulin
body text
p. 1786 - 1791
(2012/01/12)

COMPOUNDS AND METHODS FOR INHIBITING NHE-MEDIATED ANTIPORT IN THE TREATMENT OF DISORDERS ASSOCIATED WITH FLUID RETENTION OR SALT OVERLOAD AND GASTROINTESTINAL TRACT DISORDERS
The present disclosure is directed to corn- pounds and methods for the treatment of disorders associated with fluid retention or salt overload, such as heart failure (in particular, congestive heart failure), chronic kidney disease, end-stage renal disease, liver disease, and peroxisome proliferator-activated receptor (PPAR) gamma agonist-induced fluid retention. The present disclosure is also directed to compounds and methods for the treatment of hypertension. The present disclosure is also directed to compounds and methods for the treatment of gastrointestinal tract disorders, including the treatment or reduction of pain associated with gastrointestinal tract disorders. The methods generally comprise administering to a mammal in need thereof a pharmaceutically effective amount of a compound, or a pharmaceutical composition comprising such a compound, that is designed to be substantially active in the gastrointestinal (GI) tract to inhibit NHE-mediated antiport of sodium ions and hydrogen ions therein. More particularly, the method comprises administering to a mammal in need thereof a pharmaceutically effective amount of a compound, or a pharmaceutical composition comprising such a compound, that inhibits NHE-3, -2 and/ or -8 mediated antiport of sodium and/or hydrogen ions in the GI tract and is designed to be substantially impermeable to the layer of epithelial cells, or more specifically the epithelium of the GI tract. As a result of the compound being substantially impermeable, it is not absorbed and is thus essentially systemically non-bioavailable, so as to limit the exposure of other internal organs (e.g., liver, heart, brain, etc.) thereto. The present disclosure is still further directed to a method wherein a mammal is administered such a compound with a fluid-absorbing polymer, such that the combination acts as described above and further provides the ability to sequester fluid and/or salt present in the GI tract
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Page/Page column 154

(2010/08/04)

The Mannich reaction in the synthesis of N, S-containing heterocycles Recyclization of stable cyclic Michael adducts, N-methylmorpholinium 6-R-6-hydroxy-1, 4, 5, 6-tetrahydropyridine-2-thiolates, to pyrimido[4, 3-b][1, 3, 5]thiadiazines under conditions of aminomethylation reaction
5-Substituted N-methylmorpholinium 4-aryl-6-R-3-cyano-6-hydroxy-1, 4, 5, 6-tetrahydro-pyridine-2-thiolates upon the action of primary amines and HCHO in ethanol undergo recy-clization to 3, 7-disubstituted 8-aryl-3, 4, 7, 8-tetrahydro-2H, 6H-pyrimido[4, 3-b][1, 3, 5]thia-diazine-9-carbonitriles in low yields (5-28%). The latter were also obtained by alternative method, viz., by sequential condensation of cyanothioacetamide with aromatic aldehydes, primary amines, and HCHO.
Dotsenko,Frolov,Krivokolysko,Litvinov V.p.
experimental part
p. 1479 - 1483
(2011/01/06)

METHOD FOR SELECTIVELY PRODUCING PRIMARY AMINE COMPOUND
Disclosed is a method for producing a primary amine compound represented by the formula (3): wherein, Ar is as defined below , which is characterized in that a halogen compound represented by the formula (1): wherein, Ar represents an unsubstituted aromatic group such as a phenyl group, a naphthyl group, a pyridyl group, a furyl group, a thienyl group, a pyrrolyl group, an oxazolyl group, an isoxazolyl group or a pyrimidinyl group, or an aromatic group obtained by substituting such an unsubstituted aromatic group with 1-3 substituents; and X represents a halogen atom, ammonia and formaldehyde are reacted with each other, thereby obtaining a hexahydrotriazine compound represented by the formula (2): wherein, Ar is as defined above, and then the thus-obtained hexahydrotriazine compound is decomposed. By this method, a primary amine compound can be commercially advantageously produced by using a low-cost ammonia while suppressing production of a secondary amine as a by-product.
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Page/Page column 8

(2008/12/08)

Dehydroxymethylation: an unusual reverse reaction of nucleophilic addition to formaldehyde
An unusual dehydroxymethylation has been observed in an acyclic primary alcoholic system. The relief of steric congestion is considered as the primary driving force in this reaction.
Peng, Lingling,Ma, Ming,Zhang, Xiu,Zhang, Shiwei,Wang, Jianbo
p. 8175 - 8178
(2007/10/03)

Synthesis of enantiopure pyrrolidine-derived peptidomimetics and oligo-β-peptides via nucleophilic ring-opening of β-lactams
(Chemical Equation Presented) The synthesis of the two enantiomers of pyrrolidine-derived spiro β-lactams by resolution with D- and L-Boc phenylalanine is described. The potential of these optically active spiro β-lactams on the synthesis of peptidomimetics as analogues of melanostatin is evaluated. Theoretical studies of several models, at the Becke3LYP/6-31+G* level of theory, together with previous experimental evidences from our group, gathered by NMR, allow us to design structures that can efficiently mimic some biologically active peptide-type molecules. On the other hand, the spiro β-lactams have shown their utility in the preparation of β-peptides. As an example, a homo-tetra-β-peptide was synthesized. This research will continue in the future in order to obtain higher peptides with potential biological activity.
Macias, Alberto,Ramallal, Antonio Moran,Alonso, Eduardo,Del Pozo, Carlos,Gonzalez, Javier
p. 7721 - 7730
(2007/10/03)

2-(1,3,5-Dithiazinan-5-yl)ethanol heterocycles, structure and reactivity
Treatment of 2-(1,3,5-dithiazinan-5-yl)ethanol (1), 2-(1,3,5-dithiazinan-5- yl)-1-phenylethanol (2), 2-(1,3,5-dithiazinan-5-yl)-1-methylethanol (3) and 2-(1,3,5-dithiazinan-5-yl)-2-methyl-1-phenylethanol (4) with TsCl and NEt 3 in CH2Cl2 afforded the corresponding 3-tosyl-1,3-oxazolidine derivatives (5-8), whereas tosylation of 1-4 in the presence of NHMe3Cl gave the corresponding O-tosyl-2-(1,3,5- dithiazinan-5-yl)ethanol derivatives (11-14). The direct preparation of 5 and 7 from formaldehyde and N-tosylethanolamine (9) or N-tosyl-2-propanolamine was not successful. Reactions of 1 or 3 with benzylamine furnish 1,3,5-tribenzyl-1,3,5- triazinane. Heating of 1 and 2 affords the corresponding 1,3,5-tri(2- hydroxyethyl)-1,3,5-triazinanes. X-Ray diffraction studies of compounds (1-9 and 11) are reported.
Gálvez-Ruiz, Juan Carlos,Jaen-Gaspar, Javier C.,Castellanos-Arzola, Indira G.,Contreras, Rosalinda,Flores-Parra, Angelina
p. 2269 - 2285
(2007/10/03)

Dichloromethane as a Reactant in the Synthesis of 1,2,3,4-Tetrahydropyrimidine Derivatives
5-p-methoxyphenyl-1,2-dithiole-3-thione (Sulfarlem) reacts with primary amines in dichloromethane to give in good yield 1,3-dialkyl-6-methoxyphenyl-1,2,3,4-tetrahydropyrimidine-5-carbothioamides.In this reaction dichloromethane serves as a C-1 unit donor yielding, in the presence of elemental sulphur, 1,3,5-trisubstituted 1,3,5-triazanes and 3,5-disubstituted 1,3,5-thiadiazanes.These Mannich-type compounds react with enamine intermediates to give the title products.
Martens, Thierry,Souquet, Florence
p. 1671 - 1683
(2007/10/02)

Some novel routes to 1-heterosubstituted 1-vinylcyclopropanes
3-Phenylselenoalk-1-enylidene carbenes, generated in situ by base induced condensation of α-phenylseleno carbonyl compounds and diethyl diazomethylphosphonate, can be efficiently trapped by alkenes to give alkylidene-cyclopropane adducts which undergo either [1,3] allyl selenide rearrangement or oxidative selenoxide [2,3] sigmatropic rearrangement to produce 1-phenylseleno- or 1-hydroxy-1-vinylcyclopropanes respectively.
Lewis, Richard T.,Motherwell, William B.
p. 1465 - 1484
(2007/10/02)

THE MANNICH CONDENSATION WITH 1-HETERA-4-CYCLOHEXANONES. THE NOVEL FORMATION OF 7-BENZYL-3-HETERA-7-AZABICYCLONONAN-9-ONES, 3,6-DIBENZYLHEXAHYDRO-8a-METHOXY 5H-4a,8-(METHANOHETERAMETHANO)-2H-PYRIDO-1,3-OXAZINES, AND 2,4,10,12-TETRABENZYL-2,4,10,12-TETRAAZA-15-HETERADISPI...
We report for the first time the formation of unusual multicyclic products from the condensation of 1-hetera-4-cyclohexanones in a Mannich reaction with benzylamine, formaldehyde, and acetic acid in methanol.In addition to the expected ketones, namely 7-benzyl-3-hetera-7-azabicyclononan-9-ones, there were obtained from 4-thianone and 4-selenanone the following systems.Repeated Mannich condensations produced 3,6-dibenzylhexahydro-8a-(methoxy-5H-4a,8-(methanothiomethano)-2H-pyrido-1,3-oxazine, 3,6-dibenzylhexahydro-8a-methoxy-5H-4a,8-(methanoselenomethano)-2H-pyrido-1,3-oxazine, 2,4,10,12-tetrabenzyl-2,4,10,12-tetraaza-15-thiadispiro-hexadecan-7-one, and 2,4,10,12-tetrabenzyl-2,4,10,12-tetraza-15-selenadispirohexadecan-7-one.Single crystal X-ray diffraction analysis confirmed the structures of the first three solids.Using tetrahydro-4H-pyran-4-one, it was possible to obtain 7-benzyl-3-oxa-7-azabicyclononan-9-one and 2,4,10,12-tetrabenzyl-2,4,10,12-tetraaza-15-oxadispirohexadecan-7-one.To the best of our knowledge, these systems have not been previously recorded, and the method reported herein is a one-step approach.NMR analyses, including 1H, 13C, and 15N analyses, were completed and support all of the structures described herein.A mechanism is briefly outlined to explain the formation of these novel polycyclic heterocycles. - Key words: Mannich reaction; 1-hetera-4-cyclohexanones; 3,6-dibenzylhexahydro-8a-methoxy-5H-4a,8-(methanoheteromethano)-2H-pyrido--1,3-oxazine; 2,4,10,12-tetrabenzyl-2,4,10,12-tetraaza-15-heteradispirohexadecan-7-one; 7-benzyl-3-hetera-7-azabicyclononan-9-ones; selenium and sulfur derivatives.
Smith, Gary S.,Berlin, K. Darrell,Zisman, Stan A.,Holt, Elizabeth M.,Green, Vicki A.,Helm, Dick Van Der
p. 91 - 112
(2007/10/02)

Preparation of N,O-Aminals as Synthetic Equivalents of H2C=NAr and (H2C=NHAr)+ ions: Neutral- and Acid-promoted Transformations
A general method for the synthesis of N, O-aminals derived from primary aromatic amines is described.The reactivity of these compounds under neutral and acidic conditions has been studied and the title compounds can be envisaged as general purpose H2C=NAr or (H2C=NAr)+ equivalents.N,O-Aminals have been converted into perhydrotriazines by moderate heating and into bis(4-aminoaryl)methane derivatives or N-benzylarylamines, respectively, when heated in acidid media with pH control.Reduction od N,O-acetals with sodium cyanoborohydride has revealed that the C-O bond is broken exclusively in acidic media.
Barluenga, Jose,Bayon, Ana M.,Campos, Pedro,Asensio, Gregorio,Gonzalez-Nunez, Elena,Molina, Yolanda
p. 1631 - 1636
(2007/10/02)

Monoalkylation of Primary Aliphatic Amines via N-Alkyl-N-(alkylthiomethyl)ammonium Chlorides. Evidence for the Formation of Stable N-Methylenealkylamines
Monomeric N-methylenealkylamines (3), formed from N-alkyl-N-(alkylthiomethyl)ammonium chlorides (5) are stable at -60 deg C and may be trapped with organometallic reagents to provide the N,N-dialkylamines (8).
Barluenga, Jose,Bayon, Ana M.,Asensio, Gregorio
p. 427 - 428
(2007/10/02)

Enamine Chemistry. Part 27. The Effect of Additional α- and β-Heteroatoms on the p?-Conjugation and Reactivity of Enamines. Sub- or Super-Enamines?
Enamines derived from isoxazolidine and 1,3-dioxa-5-azacyclohexane have been prepared.The effect of the addition a α- or β-heteroatoms is to decrease the p?-conjugation between the nitrogen lone pair of electrons and the ?-electrons of the double bond, as reflected in the spectral properties of the enamines and their reactivity with electrophiles.The reasons for this are discussed.
Ahmed, Md. Giasuddin,Ahmed, S. Asghari,Hickmott, Peter W.
p. 2383 - 2386
(2007/10/02)