- Method for preparing diazacyclooctane intermediate and diazacyclooctane
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The invention provides a method for preparing a diazacyclooctane intermediate and diazacyclooctane. The preparation method comprises the following steps: synthesizing 1,5-bis(p-toluenesulfonyl)-1,5-diazacyclooctane from 1,3-bis(p-toluenesulfonyl)-1,3-dioxypropane, 1,3-bis(p-toluenesulfonyl)-1,3-propane diamine and sodium methoxide under a temperature condition of 60-100 DEG C; then synthesizing 1,5-diazacyclooctane bromate from 1,5-bis(p-toluenesulfonyl)-1,5-diazacyclooctane, phenol and hydroacetic acid; and finally, synthesizing 1,5-diazacyclooctane from 1,5-diazacyclooctane bromate and sodium methoxide. According to the method, the yield of the 1,5-bis(p-toluenesulfonyl)-1,5-diazacyclooctane can be increased, and the reaction time for synthesizing the 1,5-diazacyclooctane can be shortened.
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Paragraph 0019; 0023-0045
(2020/06/17)
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- Synthesis, characterization, and copper(II) chelates of 1,11-dithia-4,8-diazacyclotetradecane
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Synthesis of 1,11-dithia-4,8-diazacyclotetradecane (L1), a constitutional isomer of the macrocyclic [14]aneN2S2 series, is accompanied with reaction and method optimization. Chelation of L1 with copper(II) provided assessment of latt
- Taschner, Ian S.,Walker, Tia L.,Dehaan, Hunter S.,Schrage, Briana R.,Ziegler, Christopher J.,Taschner, Michael J.
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p. 11091 - 11102
(2019/09/30)
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- Gold-Catalyzed Regiodivergent [2 + 2 + 2]-Cycloadditions of Allenes with Triazines
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Gold-catalyzed regiodivergent cycloadditions of functionalized allenes with 1,3,5-triazines, providing diverse N-heterocycles in moderate to excellent yields under mild reaction conditions, are reported. Importantly, different types of allenes exhibit distinct selectivity and reactivity for the reactions. Mechanistic investigations reveal that all of the cycloadditions proceed through a stepwise [2 + 2 + 2]-cycloaddition process.
- Peng, Shiyong,Cao, Shengyu,Sun, Jiangtao
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supporting information
p. 524 - 527
(2017/02/10)
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- Palladium-Catalyzed Modular Synthesis of Substituted Piperazines and Related Nitrogen Heterocycles
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We report here a novel method for the modular synthesis of highly substituted piperazines and related bis-nitrogen heterocycles via a palladium-catalyzed cyclization reaction. The process couples two of the carbons of a propargyl unit with various diamine components to provide nitrogen heterocycles in generally good to excellent yields and high regio- and stereochemical control. (Chemical Equation Presented).
- Montgomery, Thomas D.,Rawal, Viresh H.
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supporting information
p. 740 - 743
(2016/03/01)
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- Tuning Side Arm Electronics in Unsymmetrical Cyclotriazadisulfonamide (CADA) Endoplasmic Reticulum (ER) Translocation Inhibitors to Improve their Human Cluster of Differentiation 4 (CD4) Receptor Down-Modulating Potencies
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Cyclotriazadisulfonamide prevents HIV entry into cells by down-modulating surface CD4 receptor expression through binding to the CD4 signal peptide. According to a two-site binding model, 28 new unsymmetrical analogues bearing a benzyl tail group and nine
- Chawla, Reena,Van Puyenbroeck, Victor,Pflug, Nicholas C.,Sama, Alekhya,Ali, Rameez,Schols, Dominique,Vermeire, Kurt,Bell, Thomas W.
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p. 2633 - 2647
(2016/04/10)
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- Synthesis and characterisation of a mesocyclic tripodal triamine ligand
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Meso- and macrocyclic polydentate amine ligands have been widely explored in oxidation catalysis and for the stabilization of unstable metal-superoxide, -peroxide, and -oxo intermediates. Herein we report on the design and synthesis of a novel mesocyclic,
- Ure, Andrew D.,Lázaro, Isabel Abánades,Cotter, Michelle,McDonald, Aidan R.
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p. 483 - 494
(2016/01/12)
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- Quantitative structure-activity relationships studies for prediction of antimicrobial activity of synthesized disulfonamide derivatives
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A new series of disulfonamides were synthesized and assayed as antimicrobial agents against Staphylococcus aureus, Bacillus cereus, and Escherichia coli. The quantitative structure-activity relationship analysis (QSAR) was applied to find out the correlat
- Alyar, Saliha,?zbek, Neslihan,Kuzuk?ran, Ku?bra,Karacan, Nurcan
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experimental part
p. 175 - 183
(2012/02/04)
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- Unsymmetrical cyclotriazadisulfonamide (CADA) compounds as human CD4 receptor down-modulating agents
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Cyclotriazadisulfonamide (CADA) inhibits HIV at submicromolar levels by specifically down-modulating cell-surface and intracellular CD4. The specific biomolecular target of CADA compounds is unknown, but previous studies led to an unsymmetrical binding model. To test this model, methods were developed for effective synthesis of diverse, unsymmetrical CADA compounds. A total of 13 new, unsymmetrical target compounds were synthesized, as well as one symmetrical analogue. The new compounds display a wide range of potency for CD4 down-modulation in CHO-CD4-YFP cells. VGD020 (IC50 = 46 nM) is the most potent CADA compound discovered to date, and VGD029 (IC50 = 730 nM) is the most potent fluorescent analogue. Structure-activity relationships are analyzed from the standpoint of additive or nonadditive energy effects of different substituents. They appear to be consistent with the zipper-type mechanism in which entropy costs are reduced for additional stabilizing interactions between the small molecule and its protein target.
- Demillo, Violeta G.,Goulinet-Mateo, Florian,Kim, Jessica,Schols, Dominique,Vermeire, Kurt,Bell, Thomas W.
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experimental part
p. 5712 - 5721
(2011/10/08)
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- A highly efficient synthesis of sulphonamide derivatives in the presence of n-methyl-2-pyrrolidone
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The sulphonamide derivatives are synthesized by two component condensation of alkyl bromide and sodium arylsulphonamide using N-methyl-2-pyrrolidone (NMP) as a reaction medium. This method results in high yields without the formation of unwanted side products, and expanding substrate scopes. Copyright
- Tan, Yong,Wang, Su Juan,Wang, Yi Ting,Gao, Bao Xiang,Ba, Xin Wu
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experimental part
p. 3648 - 3653
(2010/12/25)
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- Copper-catalyzed 1,2-double amination of 1-halo-1-alkynes. Concise synthesis of protected tetrahydropyrazines and related heterocyclic compounds
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Reaction of N,N′-di(p-toluenesulfonyl)-1,2-diamine, 1-bromo-1-alkyne, K3PO4, and a catalytic amount of CuI in hot DMF afforded N,N′-di(p-toluenesulfonyl)-1,2,3,4-tetrahydropyrazines in good yields. The reaction most likely involves (i) monoalkynylation of the diamine derivative with 1-bromo-1-alkyne, and (ii) 6-endo-dig ring closure between the acetylenic bond and another sulfonylamine moiety of the diamine. When the starting 1,2-diamine derivative was replaced with N,N′-di(p-toluenesulfonyl)-1,3-diamine or N-(p-toluenesulfonyl)-2-amino-1-ethanol, the corresponding seven-membered diazacycle or six-membered N,O-heterocycle was produced. In addition, 1,1-dibromo-1-alkene could be used in place of 1-bromo-1-alkyne. Copyright
- Fukudome, Yasuhiro,Naito, Hiroyuki,Hata, Takeshi,Urabe, Hirokazu
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p. 1820 - 1821
(2008/09/18)
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- Synthesis of 2-substituted 1-tosyl-3-(1-tosyliminoalkyl)imidazolidines and-hexahydropyrimidines
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Reactions of N-tosylimidoyl chlorides with the Schiff bases of the general formula TsNH(CH2)nN=CHR (n = 2 or 3; R = Pri, 4-MeOC6H4, 4-Me2NC6H4, and 3-O2NCs
- Pokhvisneva,Luk'Yanov
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p. 903 - 906
(2007/10/03)
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- Facile and chemoselective microwave-assisted cleavage of oximes to their corresponding carbonyl compounds using N,N′-dibromo-N,N′-1,3- propylene-bis[(4-methylphenyl)sulfonamide] as a deoximating reagent
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Aldoximes and ketoximes are converted to the parent carbonyl compounds in good yields when treated with N,N′-dibromo-N,N′-1,3-propylene- bis[(4-methylphenyl)sulfonamide] (2) under microwave irradiation. The simple workup minimizes the loss of product and oximes have been selectively oxidized in the presence of alcohols and alkenes.
- Khazaei, Ardeshir,Manesh, Abbas Amini,Ghasemi, Amir Hoshang
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p. 2784 - 2786
(2007/10/03)
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- Design and synthesis of pyrrolo[2,1-c][1,4]benzodiazepine (PBD)- polyaminoalkyl conjugates by the use of SNAr reaction of 2-nitro-5-fluorobenzoate precursor as key reaction
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The design and synthesis of a series of pyrrolo[2,1-c][1,4]benzodiazepine (PBD)- polyaminoalkyl conjugates as DNA minor groove binders are described. To introduce polyaminoalkyl groups to the pyrrolo[2,1-c][1,4]benzodiazepine pharmacophore, SNA
- Iida, Hirokazu,Hayashi, Naoto,Lown, J. William,Matsumoto, Kiyoshi
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p. 693 - 711
(2007/10/03)
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- Synthesis of polyaminoalkyl substituted conjugates of pyrrolo[2,1- c][1,4]benzodiazepine involving S(N)Ar reaction of 2-nitro-5-fluorobenzoate precursors
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A synthetic procedure is described for conjugating polyaminoalkyl groups to the pyrrolo[2,1-c][1,4]benzodiazepine pharmacophore in order to alter its characteristic DNA sequence binding preference. To this end S(N)Ar reactions of 2-nitro-5-fluorobenzoate
- Matsumoto, Kiyoshi,Iida, Hirokazu,Lown, J. William
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p. 1015 - 1020
(2007/10/03)
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- 84. Selective Monoderivatization of Propane-1,3-diamine with Acid Chlorides: 'Hexahydropyrimidine Method' vs. Statistic Methods
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The selective N-monoderivatization of propane-1,3-dmmine (5) with carbonyl and sulfonyl chlorides via 2-phenylhexahydropyrimidine (6) was compared with the direct statistic monoderivatization. It was found that, under optimized conditions, both methods ar
- Jentgens, Christian,Bienz, Stefan,Hesse, Manfred
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p. 1133 - 1143
(2007/10/03)
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- Condensation of Alkanediamines with Formaldehyde; Intramolecular Disproportionation of N-Hydroxymethyl Groups into N-Methyl and N-Formyl Groups
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The condensation of α,ω-alkanediamines NH2(CN2)nNH2 with aqueous formaldehyde has been studied by NMR spectroscopy of isolated products and of product mixtures.The condensation was reversible and gave products of widely different types depending on alkane chain length: bicyclic oxadiaza compounds (n = 2, 3, 4), a tricyclic tetraaza compound (n = 2), a quinquecyclic octaaza compound (n = 3), two-dimensional polymers (n = 4, 5).A slow irreversible rearrangement gave in two cases (n = 3, 4), unicyclic 1-formyl-3-methyl-1,3-diaza compounds.The condensation of N,N'-dimethyl-α,ω-alkandediamines CH3NH(CH2)nNHCH3 with aqueous formaldehyde was also studied.The reversible formation of simple unicyclic diaza compounds was observed in all cases (n = 2, 3, 4), but in one case (n = 2) there was again a slow irreversible rearrangement to the N-formyl-N,N'N'-trimethyl derivative.The rearrangement reaction involves a hydride shift and is strictly intramolecular.The conditions for its occurrence can be understood on a conformational basis.
- Dale, Johannes,Sigvartsen, Turid
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p. 1064 - 1070
(2007/10/02)
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- MACROCYCLIC AND MACROPOLYCYCLIC COMPOUNDS BASED UPON 1,3-DISUBSTITUTED PROPANE UNITS
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Synthetic routes to the macrocyclic polyamine derivatives (1) and (3) are described, together with an investigation of the complexing properties of the triamines (1d) and (3d) with primary alkylammonium cations.Macrotricyclic and macrotetracyclic compounds may be obtained from the macrocycle (1) by a stepwise procedure whereas macrocycle (3b) can be converted into a macrotricyclic derivative in a one step alkylation procedure.The alkylation of the tetrahydropyrimidone (18) with α,α'-dibromo-m-xylene gives the calix arene analogue (19) which adopts the 'cone' (21a) and '1,3-alternate' (21b) conformations.The macrocyclic hexa-amine (23) may be synthesized by a simple alkylation procedure whereas the octa-amine (27) required a systematic stepwise synthesis.The hexa-amine salt (23)*6 HBr shows selectivity in forming inclusion complexes with the dicarboxylate anions (1-)O2C(CH2)nCO2(1-).
- Pratt, John A. E.,Sutherland, Ian O.,Newton, Roger F.
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- A THERMOMETRIC TITRIMETRIC STUDY OF THE COMPLEXATION OF ALKALINE-EARTH METALS BY MACROCYCLIC POLY(AMINOCARBOXYLIC) ACIDS
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Thermometric titrimetry has been employed to determine K, ΔH and ΔS data for the complexation reaction in aqueous solution of 1,4-piperazine-N,N'-diacetic acid, 1,5-diazacyclooctane-N,N'-diacetic acid, 1-oxa-4,7-diazacyclononane-N,N'-diacetic acid, 4-oxa-1,7-diazacyclodecane-N,N'-diacetic acid and 1,11-dioxa-4,8-diazacyclotridecane-N,N'-diacetic acid with alkaline earth metal cations.Factors influencing the thermodynamic stability of these complexes are discussed.
- Ewin, Gavin,Hill, John O.
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p. 3501 - 3519
(2007/10/02)
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- Improved Richman-Atkins Syntheses of Cyclic Polyamines Particularly 1,4,7-Triazacyclononane (tacn) and 1,4,7-Triazacyclodecane (tacd), with the Aid of Cation-Exchange in Purification and Isolation
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Richman-Atkins cyclization syntheses for the cyclic triamines 1,4,7-triazacyclononane (tacn) and 1,4,7-triazacyclodecane (tacd) with the alternative possible sets of reagents asd tosyl derivatives have been examined in detail and compared.The cyclizations from the tritosyl derivative of diethylenetriamine (dientt) and the appropriate diols as ditosylates proceeded relatively cleanly, although there were small amounts of higher products and some carry through of dientt for tacn.The alternative cyclizations, from 2,2'-(tosylimino)bisethyl ditosylate and a ditosyl diamine, gave little reaction to form tacn as the tritosyl derivative.The reaction to form tritosyl tacd proceeded further, but was accompanied by significant formation of higher condensation products, particularly the hexamines 1,4,7,11,14,17-hexaazacycloeicosane (2:2 cyclic dimer) and 3,7,10,13-tetraazahexadecane-1,16-diamine.A cation-exchange procedure, applied after the detosylation stage, is described for obtaining the required pure 1 : 1 cyclic polyamines as their hydrochloride salts with high recovery.This is an effective method for removing higher co-products.These may be recovered, and by this means the above hexamines were isolated in admixture.
- Searle, Graeme H.,Geue, Rodney J.
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p. 959 - 970
(2007/10/02)
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- 123. Synthesis and Protonation Features of 24-, 27- and 32-membered Macrocyclic Polyamines
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Three macrocyclic polyamines ane-N6 1, ane-N8 2 and ane-N6O3 3 of ring size 24, 32 and 27, respectively, have been synthesized.They contain either trimethylenediamine of ethylenediamine units.The acyclic analog 4, as the reference compound, wa
- Dietrich, Bernard,Hosseini, Mir Wais,Lehn, Jean-Marie,Sessions, Richard B.
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p. 1262 - 1278
(2007/10/02)
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- Preferential Introduction of a Pyridylmethyl Group into Sulfonamides as an Approach to an Intramolecular Transimination
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N,N'-Bis(p-tolylsulfonyl)-α,ω-alkanediamine disodium salts (n=3, 4, 5, 6, 7, 8, 9, 10) were subjected to monopyridylmethylation by the reaction with 5'-deoxy-5'-chloro- or 5'-deoxy-2'-chloro-3,4'-O-isopropylidenepyridoxine hydrochloride, accompanied by th
- Iwata, Masaaki,Kuzuhara, Hiroyoshi
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p. 2153 - 2157
(2007/10/02)
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- Dynamic Protection of Amines using 18-Crown-6
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The regioselectivity of diamine monoacylation has been controlled by selective complexation with 18-crown-6 and a proton source.
- Barrett, Anthony G. M.,Lana, J. Carlos A.,Tograie, Shahrzad
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p. 300 - 301
(2007/10/02)
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