- Bis(benzylamine) monomers: One-pot preparation and application in dendrimer scaffolds for removing pyrene from aqueous environments
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Bisimine and bisamine AB2 monomers have been synthesized from 3,5-diaminobenzoic acid and benzaldehyde derivatives without the need for protective groups or purification. This monomer preparation is universal for various electron-donating and electronwith
- Monaco, Olivia N.,Tomas, Sarah C.,Kirrane, Meghan K.,Balija, Amy M.
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Read Online
- Cannabidiol derivative and preparation method thereof
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The invention provides a cannabidiol derivative and a preparation method thereof. According to the cannabidiol derivative provided by the invention, a specific structure as shown in a formula I is formed by improving a benzyl substituent and a side chain on the basis of CBD, so that the anti-inflammatory effect of the cannabidiol derivative can be improved, and the toxicity can be reduced.
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Paragraph 0166-0171
(2021/06/06)
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- Design and synthesis of π-extended resveratrol analogues and in vitro antioxidant and anti-inflammatory activity evaluation
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The research on resveratrol (1) has been conducted intensively over a long time due to its proven antioxidant activity and disease-fighting capabilities. Many efforts have also been made to increase these biological effects. In the present study, six new extended aromatic resveratrol analogues containing naphthalene (2) and its bioisosteres quinoline (3 and 4), isoquinoline (5) quinoxaline (6) and quinazoline (7) scaffolds were designed and synthesized using an annulation strategy. The antioxidant and anti-inflammatory activities of these compounds were investigated. All compounds showed better antioxidant activity than resveratrol in ABTS assay. As for the anti-inflammatory test, 5 and 7 exhibited better activity than resveratrol. It is worth noting that nitrogen substitution on the extended aromatic resveratrol analogues has a significant impact on cell viability. Taking the antioxidant activities and NO inhibition activities into consideration, we conclude that isoquinoline analogue 5 may qualify for the further investigation of antioxidant and anti-inflammatory therapy. Furthermore, our study results suggest that in order to improve the biological activity of polyphenolic compounds, extended aromaticity and nitrogen substitution strategy could be a viable method for the design of future drug candidates.
- Damodar, Kongara,Gim, Ji Geun,Jeon, Seong Ho,Lee, Jeong Tae,Lee, Yeontaek,Nam, Ki Yoon,Park, Jae Phil,Park, Lee Seul
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- Synthetic method for dihydrostilbenes and anti-inflammatory compounds containing thereof
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The present invention aims to provide an effective anti-inflammatory agent without side effects. The present inventors have invented a method for efficiently synthesizing dihydrostilbene and derivatives (compounds 1 to 5) from starting materials at a high yield. In addition, the anti-inflammatory effects were evaluated in LPS-induced RAW-264.7 macrophages. The compounds of dihydrostilbene do not exhibit cytotoxicity and are shown to weakly or well inhibit nitric oxide production induced by LPS at the concentration of 10 andmu;M.COPYRIGHT KIPO 2018
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Paragraph 0104; 0111-0113; 0116; 0124; 0125
(2018/05/03)
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- CO2-Catalyzed oxidation of benzylic and allylic alcohols with DMSO
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CO2-catalyzed transition-metal-free oxidation of alcohols has been achieved. Earlier, several methodologies have been explored for alcohol oxidations based on transition-metal catalysts. However, owing to the cheaper price, easy separation and nontoxicity, transition-metal-free systems are in high demand to the pharmaceutical industries. For this reason, various primary and secondary alcohols have been selectively oxidized to the corresponding carbonyl compounds using CO2 as a catalyst in the presence of different functional groups such as nitrile, nitro, aldehyde, ester, halogen, ether, and so on. At the end, transition-metal-free syntheses of pharmaceuticals have also been achieved. Finally, the role of CO2 has been investigated in detail, and the mechanism is proposed on the basis of experiments and DFT calculations.
- Riemer, Daniel,Mandaviya, Bhavdip,Schilling, Waldemar,G?tz, Anne Charlotte,Kühl, Torben,Finger, Markus,Das, Shoubhik
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p. 3030 - 3034
(2018/04/14)
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- Practical Aerobic Oxidation of Alcohols: A Ligand-Enhanced 2,2,6,6-Tetramethylpiperidine-1-oxy/Manganese Nitrate Catalyst System
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A highly efficient, ligand-enhanced 2,2,6,6-tetramethylpiperidine-1-oxy (TEMPO)/Mn(NO3)2 catalyst system for the aerobic oxidation of alcohols is described. From the series of coordinating ligands studied herein, 2-picolinic acid (PyCOOH) improves the catalytic activity of TEMPO/Mn(NO3)2 remarkably. Under ambient air at room temperature in acetic acid, the ligand-enhanced catalyst converts aliphatic and benzylic primary alcohols that bear various functional groups into their respective aldehydes with near quantitative conversions. The applicability of the catalyst for convenient preparative synthesis was demonstrated by conducting oxidations on a gram scale. A change of TEMPO to the sterically less demanding 9-azabicyclo[3.3.1]nonane N-oxyl results in a Mn catalyst that is also able to oxidize secondary alcohols to ketones. Mechanistic studies showed that alcohols are oxidized by the oxoammonium cation derived from the nitroxyl radical. The active oxidant is regenerated by Mn(NO3)2, and this process is greatly promoted by the coordination of PyCOOH to Mn.
- Lagerblom, Kalle,Lagerspets, Emi,Keskiv?li, Juha,Cook, Chris,Ekholm, Filip,Parviainen, Arno,Repo, Timo
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p. 3880 - 3887
(2017/09/28)
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- Dihydrostilbenes and diarylpropanes: Synthesis and in vitro pharmacological evaluation as potent nitric oxide production inhibition agents
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An efficient synthesis of dihydrostilbenes (1–5) and diarylpropanes (6–10) is achieved from the commercially available starting materials and Wittig-Horner reaction, Claisen–Schmidt condensation and hydrogenation as key steps. Later, their nitric oxide (NO) production inhibition effects were evaluated in lipopolysaccharide (LPS)-induced RAW-264.7 macrophages as an indicator of anti-inflammatory activity. All the tested compounds significantly decreased NO production in a concentration-dependent manner except compounds 2, 6 and 8 and did not show notable cytotoxicity except compound 1. Two compounds i.e., compound 9 (hindsiipropane B) (100%; IC50?=?1.84?μM) possessed the most potent NO inhibitory activity which was even stronger than the positive control, L-NMMA (90.1%; IC50?=?2.73?μM) followed by compound 4 (75.5%; IC50?=?2.98?μM) at 10?μM concentration and this finding was also further correlated by suppressed expression of LPS stimulated inducible NO synthase. Our study revealed that compound 9, a 1,3-diarylpropane scaffold with 3″,4″-dimethoxyphenyl and 3′,4′-dihydroxy-2′-methoxyphenyl motifs could be considered as potential compound or lead compound for further development of NO production-targeted anti-inflammatory agents.
- Jang, Ha Young,Park, Hyeong Jin,Damodar, Kongara,Kim, Jin-Kyung,Jun, Jong-Gab
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supporting information
p. 5438 - 5443
(2016/11/09)
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- Flexible analogues of WAY-267,464: Synthesis and pharmacology at the human oxytocin and vasopressin 1a receptors
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A previously identified, non-peptidic oxytocin (OT) receptor agonist WAY-267,464 (1) and nine novel derivatives (3, 4a-7a, 4b-7b) were synthesised and evaluated in vitro with the aim of systematically exploring hydrogen bonding interactions and ligand flexibility. All analogues were subjected to competition radioligand binding assays at human oxytocin (OT) and arginine vasopressin 1a (V1a) receptors. Physiological activity was determined using whole cell IP1 accumulation assays. Under these conditions, WAY-267,464 had higher affinity for the V1a receptor compared to the OT receptor (8.5x more selective) with poor functional selectivity (2x selective for OT receptor agonism over V1a receptor antagonism). Methylation of the resorcinol moiety (3) reversed the OT receptor pharmacological profile, removing agonist activity and inducing antagonist activity, without altering V1a receptor pharmacology. All flexible tethered derivatives removed OT receptor affinity and activity resulting in the generation of highly selective V1a receptor ligands.
- Jorgensen, William T.,Gulliver, Damien W.,Werry, Eryn L.,Reekie, Tristan,Connor, Mark,Kassiou, Michael
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p. 730 - 740
(2016/01/09)
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- Design, synthesis and SAR study of hydroxychalcone inhibitors of human β-secretase (BACE1)
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According to the structural characteristics of isoliquiritigenin from Glycyrrhiza uralensis, a series of hydroxychalcones has been designed, synthesized and evaluated for their in vitro inhibitory activities of β-secretase (BACE1). Structure-activity relationship study suggested that inhibitory activity against BACE1 was governed to a greater extent by the hydroxyl substituent on A-and B-ring of the chalcone, and the most active compound was substituted with four hydroxyl group (17, IC50=0.27 μM).
- Ma, Lei,Yang, Zhengyi,Li, Chenjing,Zhu, Zhiyuan,Shen, Xu,Hu, Lihong
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experimental part
p. 643 - 648
(2012/04/10)
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- Synthesis of organometallic poly(dendrimer)s by macromonomer polymerization: effect of dendrimer size and structural rigidity on the polymerization efficiency
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Two series of first to third generation (G1-G3) oligoether dendrimers, one hearing a shorter spacer chain (C-O) and the other having a longer spacer branch (C-C-C-O) were prepared. Both series of compounds, containing two reactive C≡CH moieties on the dendrimer surface, were used as macromonomers and copolymerized with trans-[Pt(PEt3)2Cl2] to form organometallic poly(dendrimer)s by an outer-sphere-outer-sphere connection strategy. It was found that concentration of monomer used in the polymerization, the dendrimer generation, and, most strikingly, the length of the spacer were key factors that determined the polymerization efficiency. Hence, the structurally more rigid and compact C-O linked dendrimers formed poly(dendrimer)s with a higher degree of polymerization than the structurally less rigid and more bulky C-C-C-O dendrimers. This result was due to the higher tendency to form cyclic oligomers in the latter series of compounds. In addition, the differences in the polymerization efficiency among the three generations of dendrimers could be explained by the gradual decrease of reactive functional group density on the dendrimer surface.
- Cheung, Siu-Yin,Chow, Hak-Fun,Ngai, To,Wei, Xiaoling
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supporting information; experimental part
p. 2278 - 2288
(2009/10/23)
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- Total synthesis of (S)-(-)-curvularin: A ring-closing-metathesis-based construction of the macrocyclic framework
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A convergent, flexible, and efficient approach to the synthesis of curvularin is described. Key step is the high-yielding macrocyclic ring formation by ring-closing metathesis (RCM) using the Grubbs second-generation catalyst. Georg Thieme Verlag Stuttgar
- Mohapatra, Debendra K.,Rahaman, Hasibur,Pal, Rita,Gurjar, Mukund K.
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scheme or table
p. 1801 - 1804
(2009/04/08)
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- Synthesis and retrostructural analysis of libraries of AB3 and constitutional isomeric AB2 phenylpropyl ether-based supramolecular dendrimers
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We report the synthesis of methyl esters of 3-(4-hydroxyphenyl)propionic, 3-(3,4-dihydroxyphenyl)propionic, 3-(3,5-dihydroxyphenyl)propionic, and 3-(3,4,5-trihydroxyphenyl)propionic acids and their use in a convergent iterative strategy to prepare up to four generations of three libraries, one of 3,4,5- and two of constitutional isomeric 3,4- and 3,5-substituted 3-phenylpropyl dendrons. Each library contains 3-[3,4,5-tris(dodecyl-1-oxy) phenyl]propyl-, 3-[3,4-bis(dodecyl-1-oxy)phenyl]propyl-, 3-{3,4-bis[3-(4- dodecyl-1-oxyphenyl)propyl-1-oxy]phenyl}propyl-, and 3-{3,4,5-tris[3-(4-dodecyl- 1-oxyphenyl)propyl-1-oxy]phenyl}propyl ether first-generation dendrons on their periphery and -CO2CH3, -COOH, and -CH2OH groups at their apex. Regardless of their generation number and their periphery, internal, and apex structures, these dendrons self-assemble into supramolecular dendrimers that self-organize into all periodic and quasi-periodic assemblies encountered previously and in several unencountered with architecturally related benzyl ether-based supramolecular dendrimers. A variety of porous columnar lattices that were previously obtained only from dendritic dipeptides and hollow supramolecular spheres were also discovered from these building blocks. The more flexible and less compact 3-phenylpropyl ether repeat units are stable under acidic conditions, facilitate a simpler synthetic strategy, provide faster dynamics of self-assembly into higher-order supramolecular structures of larger dimensions, exhibit lower transition temperatures than the corresponding benzyl ether homologues, and demonstrate the generality of the self-assembly concept based on amphiphilic dendrons.
- Percec, Virgil,Peterca, Mihai,Sienkowska, Monika J.,Ilies, Marc A.,Aqad, Emad,Smidrkal, Jan,Heiney, Paul A.
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p. 3324 - 3334
(2007/10/03)
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- Synthesis of versatile intermediates of the ferrocene series: Reductive amination of ferrocenecarbaldehyde
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Reductive amination of ferrocenecarbaldehyde with several primary and secondary amines in the presence of sodium triacetoxyborohydride was studied. This method was used for the synthesis of new ferrocenylmethylamines, viz., N-(ferrocenylmethyl)isoleucine methyl ester, N,N-bis(ferrocenylmethyl)glycine ethyl ester, and N-(3,5-dibenzyloxybenzyl)-N-(ferrocenylmethyl)methylamine. The latter is a potential precursor of a dendrimer with the chiral ferrocenyl plane in the core.
- Khrushcheva,Sokolov
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p. 830 - 833
(2007/10/03)
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- Dendronized protein polymers: Synthesis and self-assembly of monodisperse cylindrical macromolecules
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Monodisperse dendronized protein polymers (DPPs), cylindrical dendrimers containing protein core, can be efficiently produced through a combined modular biosynthetic strategy. These DPP materials possess predictable size, shape, and solubility. In organic
- Zhuravel, Michael A.,Davis, Nicolynn E.,Nguyen, SonBinh T.,Koltover, Ilya
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p. 9882 - 9883
(2007/10/03)
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- A new convergent approach to dendritic macromolecules
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The novel convergent growth approach to dendritic macromolecules is described. Polyether dendritic sectors [G-na]-OH from the first to the fourth generations, respectively, were prepared by this approach from readily available starting material.
- Cao, Xiaoping,Wang, Feng,Guo, Shu
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p. 3149 - 3158
(2007/10/03)
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- End-cap stabilized oligoynes: Model compounds for the linear sp carbon allotrope carbyne
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Three series of differently 3,5-disubstituted α,ω-diphenylpolyynes Ar-(C≡C)n-Ar (n=2, 4, 6, 8, 10) were synthesized under optimized Cadiot - Chodkiewicz conditions, isolated and completely characterized. These compounds can be considered as mod
- Gibtner, Thomas,Hampel, Frank,Gisselbrecht, Jean-Paul,Hirsch, Andreas
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p. 408 - 432
(2007/10/03)
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- Isoquinoline compound melanocortin receptor ligands and methods of using same
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The invention relates to melanocortin receptor ligands and methods of using the ligands to alter or regulate the activity of a melanocortin receptor. The invention further relates to tetrahydroisoquinoline aromatic amines that function as melanocortin receptor ligands and as agents for controlling cytokine-regulated physiologic processes and pathologies, and combinatorial libraries thereof.
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- Oxoammonium salts. 6. 4-Acetylamino-2,2,6,6-tetramethylpiperidine-1- oxoammonium perchlorate: A stable and convenient reagent for the oxidation of alcohols. Silica gel catalysis
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4-Acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate, 1, is a stable, nonhygroscopic oxoammonium salt that is easily prepared and can be used for the oxidation of alcohols to ketones or aldehydes in near quantitative yields. The reaction is colorimetric, does not require anhydrous conditions, does not involve heavy metals, and can be carried out conveniently. Furthermore, the oxidant can be easily regenerated. The oxidation is somewhat specific in that the relative reactivities of an allyl alcohol (geraniol), benzaldehyde, and 1-decanol are about 100:1:0.1. The reaction is catalyzed by silica gel.
- Bobbitt, James M.
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p. 9367 - 9374
(2007/10/03)
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- Benzimidazolium dichromate - A new reagent for selective oxidation under microwave irradiation
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Benzimidazolium dichromate (BIDC), is conveniently prepared and functions as a selective reagent for the oxidation of benzylic and allylic alcohols to the corresponding carbonyl compounds under microwave irradiation.
- Meng, Qing-Hua,Feng, Jun-Cai,Bian, Ning-Sheng,Liu, Bin,Li, Chang-Chuan
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p. 1097 - 1102
(2007/10/03)
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- Asymmetric Synthesis of a Series of Chiral AB2 Monomers for Dendrimer Construction
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Efficient preparation of a series of four chiral, nonracemic AB2 monomers suitable for the construction of dendrimers is presented. Monomers 1-4 possess the common structural features of a diphenolic moiety and a benzylic or aliphatic hydroxyl which render these molecules suitable for convergent dendrimer synthesis. The same basic, high-yielding, five-step sequence is employed for 1-4. Stilbene derivatives 13 and 14 are prepared by a Horner-Wadsworth-Emmons modified Wittig reaction between 3,5- or 3,4-bis(benzyloxy)benzaldehyde (8 and 10) and an ester-substituted benzylphosphonate (11 or 12). Cinnamate derivatives 21 and 22 are prepared similarly from 8 and 10 and triethyl phosphonoacetate. Chirality is introduced in the form of a 1,2-diol unit by Sharpless asymmetric dihydroxylation (AD) (>97% ee in all cases). Protection of the 1,2-diols as their acetonide derivatives provides dioxolane intermediates 17, 18, 25, and 26. Reduction of the ester groups followed by hydrogenolysis of the benzyl ethers yields AB2 monomers 1-4 in 57-67% overall yield from 8 and 10.
- McElhanon, James R.,Wu, Mu-Jen,Escobar, Maya,Chaudhry, Umer,Hu, Chun-Ling,McGrath, Dominic V.
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p. 908 - 915
(2007/10/03)
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- Arylamide inhibitors of HIV-1 integrase
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Based on data derived from a large number of HIV-1 integrase inhibitors, similar structural features can be observed, which consist of two aryl units separated by a central linker. For many inhibitors fitting this pattern, at least one aryl ring also requires orth obis-hydroxylation for significant inhibitory potency. The ability of such catechol species to undergo in situ oxidation to reactive quinones presents one potential limitation to their utility. In an effort to address this problem, a series of inhibitors were prepared which did not contain ortho bishydroxyls. None of these analogues exhibited significant inhibition. Therefore an alternate approach was taken, whose aim was to increase potency rather than eliminate catechol substructures. In this latter study, naphthyl nuclei were utilized as aryl components, since a previous report had indicated that fused bicyclic rings may afford higher affinity relative to monocyclic phenyl-based systems. In preliminary work with monomeric units, it was found that the 6,7-dihydroxy- 2-naphthoic acid (17) (IC50 = 4.7 μM) was approximately 10-fold more potent than its 5,6-dihydroxy isomer 19 (IC50 = 62.4 μM). Of particular note was the dramatic difference in potency between free acid 17 and its methyl ester 21 (IC50 > 200 μM). The nearly total loss of activity induced by esterification strongly indicates that the free carboxylic -OH is important for high potency of this compound. This contrasts with the isomeric 5,6-dihydroxy species 19, where esterification had no effect on inhibitory potency (23, IC50 = 52.7 μM). These data provide evidence that the monomeric 6,7- and 5,6-dihydroxynaphthalenes may be interacting with the enzyme in markedly different fashions. However, when these naphthyl nuclei were incorporated into dimeric structures, significant enhancements in potencies each relative to the monomeric acids were observed, with bis-6,7- dihydroxy analogue 49 and bis-5,6-dihydroxy analogue 51 both exhibiting approximately equal potencies (IC50 values of 0.81 and 0.11 μM, respectively).
- Zhao, He,Neamati, Nouri,Mazumder, Abhijit,Sunder, Sanjay,Pommier, Yves,Burke Jr., Terrence R.
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p. 1186 - 1194
(2007/10/03)
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- Induction of liquid crystallinity by host-guest interactions
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A molecular clip is described which binds aromatic guests by an induced fit mechanism. It contains twelve long aliphatic chains and can evoke liquid-crystalline properties in a variety of molecules, including polymers and porphyrins, by a process of molecular recognition.
- Van Nunen, Johanna L. M.,Folmer, Brigitte F. B.,Nolte, Roeland J. M.
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p. 283 - 291
(2007/10/03)
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- Synthesis of porphyrins tailored with eight facially-encumbering groups. An approach to solid-state light-harvesting complexes
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Synthetic models of the photosynthetic antenna complexes must achieve long-range 3-dimensional order encompassing a large number of porphyrinic pigments with limited direct contact of the pigments. In order to develop solid-state antenna complexes, we have synthesized porphyrins bearing benzyloxy groups projecting over both faces and optionally also around the periphery of the porphyrin. Routes have been established for prefunctionalizing benzaldehydes with various benzyloxy groups. Reaction of 2,6-bis, 3,5-bis, or 2,4,6-tris(benzyloxy)benzaldehydes with pyrrole via the room temperature two-step one-flask porphyrin reaction provides direct access to the facially-encumbered porphyrins. The benzyloxybenzaldehydes react as efficiently as methoxybenzaldehydes, indicating the utility of the -OCH2- unit for introducing large substituents near the face of the porphyrin. The octakis and dodecakis(benzyloxy)porphyrins exhibit characteristic porphyrin absorption and fluorescence properties in solution. The crystal structure of meso-tetrakis[2,6-bis(2,3,4,5,6-pentalfuorobenzyloxy)phenyl]porphyrin has been determined. The pentafluorobenzyloxy substituents provide a cavity on each side of the porphyrin plane which has an approximate cylindrical shape with a diameter of ~7.5 A and a height of ≥4.5 A. The porphyrin core parameters are those obtained for free base derivatives in which the inner hydrogen atoms are ordered. Crystal data: a=14.759 (1) A, b=25.519 (2) A, c=13.100 (1) A, α=100.04 (1), β=99.83 (1), γ=88.25 (1), V=4767.3 (6) A3, all measurements at 127 K, triclinic, space group P1, Z=2 R1(F)=0.097, for 10020 'observed' data, and wR2(F2)=0.275 for 17761 total unique (all) data.
- Wagner,Wagner, Richard W.,Lindsey,Lindsey, Jonathan S.,Turowska-Tyrk,Turowska-Tyrk, Ilona,Scheidt,Scheidt, W. Robert
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p. 11097 - 11112
(2007/10/02)
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- Synthesis and Protein-Tyrosine Kinase Inhibitory Activity of Polyhydroxylated Stilbene Analogues of Piceatannol
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A series of hydroxylated trans-stilbene related to the antileukemic natural product trans-3,3',4,5'-tetrahydroxy stilbene (piceatannol) (1) has been prepared and tested for inhibition of the lymphoid cell lineage-specific protein-tyrosine kinase p56lck, which plays an important role in lymphocyte proliferation and immune function.A number of the analogues displayed enhanced enzyme inhibitory activity relative to the natural product.Reduction of the double bond bridging the two aromatic rings and benzylation of the phenolic hydroxyl groups was found to decrease activity significantly.The most potent compounds in the series proved to be trans-3,3',5,5'-tetrahydroxystilbene, trans-3,3',5-trihydroxystilbene, and trans-3,4,4'-trihydroxystilbene.
- Thakkar, Kshitij,Geahlen, Robert L.,Cushman, Mark
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p. 2950 - 2955
(2007/10/02)
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- 2-(β-Arylethylamino)- and 4-(β-Arylethylamino)quinazolines as Phosphodiesterase Inhibitors
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The existence of several forms of cAMP phosphodiesterase having different kinetic characteristics suggests the feasibility of developing tissue-selective inhibitors of this enzyme.This observation is of particular importance in the development of therapeutic agents for the management of reversible obstructive airways disorders.The present report describes the design, synthesis and pharmacological characterization of a series of 6,7-dimethoxyquinazoline derivatives having β-arylethylamine substituents at the 2- or 4- positions.The quinazoline nucleus is intended to confer a high degree of inhibitory activity for phosphodiesterase while the β-arylethylamine moieties are designed to provide selectivity for adrenergically innervated tissue.The target compounds of this study, 6 and 7 were prepared via β-arylethylamine displacement of chloride from an appropriate chloroquinazoline intermediate.The resulting products were evaluated for their ability to relax guinea pig tracheal smooth muscle and as inhibitors of phosphodiesterase.
- Millen, J.,Riley, T. N.,Waters, I. W.,Hamrick, M. E.
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- Aromatic Hydroxylation. Hydroxybenzaldehydes from Bromobenzaldehydes via Reaction of in Situ Generated, Lithiated α-Morpholinobenzyl Alkoxides with Nitrobenzene
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A general method for the one-step conversion of bromobenzaldehydes to the corresponding hydroxybenzaldehydes has been developed.The method involves in situ protection of the aldehyde function of the bromobenzaldehyde as its lithium morpholinoalkoxide, followed by lithium-bromine exchange, reaction with nitrobenzene at -75 deg C, and a subsequent acidic workup.The method has been applied to the synthesis of 4,5-dimethoxy-3-hydroxy- (1a), 3,5-dimethoxy-2-hydroxy- (2a), 3,5-bis(benzyloxy)-2-hydroxy- (2b), 3,4-dimethoxy-2-hydroxy- (14), 3-hydroxy-4,5-(methylenedioxy)- (16), and 4,5-dimethoxy-2-hydroxybenzaldehydes (18) from the bromobenzaldehydes 4, 12a, 12b, 13, 15, and 17, respectively.
- Sinhababu, Achintya K.,Borchardt, Ronald T.
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p. 1941 - 1944
(2007/10/02)
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- Synthesis of Cannabinoid Model Compounds. Part 2): (3R,4R)-δ1(6)-Tetrahydrocannabinol-5"-oic Acid and 4"(R,S)-Methyl-(3R,4R)-δ1(6)-Tetrahydrocannabinol-5"-oic Acid
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Two novel cannabinoid model compounds, (3R,4R)-Δ1(6)-tetrahydrocannabinol-5"-oic acid (22) and 4"(R,S)-methyl-(3R,4R)-Δ1(6)-tetrahydrocannabinol-5"-oic acid (23) were synthesized by acid-catalyzed condensation of (+)-trans-p-mentha-2,8-dien-1-ol (1) with the substituted resorcinols 18 and 19 obtained by a Wittig reaction between 3,5-bis(benzyloxy)benzaldehyde (7) and methyl 4-bromobutanoate (10) or methyl 4-bromo-2(R,S)-methylbutanoate (11) resp. with subsequent hydrogenation.The resulting methyl esters 20 and 21 were hydrolyzed to give acids 22 and 23.
- Franke, Ingo,Binder, Michael
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p. 2508 - 2514
(2007/10/02)
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