- Enantioselective bioreduction of benzo-fused cyclic ketones with engineered: Candida glabrata ketoreductase 1-a promising synthetic route to ladostigil (TV3326)
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Biocatalysis has been recently emerging as a promising alternative to traditional chemical synthesis because of its "green" characteristics and comparable selectivities, which accord with the concept of sustainable development and demand for asymmetric synthesis. In this study, whole-cell biocatalysts containing glucose dehydrogenase (GDH) and Candida glabrata ketoreductase 1 (CgKR1) variants were constructed. These biocatalysts were applied to the reduction of benzo-fused cyclic ketones and showed good to high activities and enantioselectivities. Particularly, CgKR1 variants displayed high activities (90.6%-98.4% conversions) and enantioselectivities (>99.9% ee) towards 5a, a key intermediate of ladostigil (TV3326). Based on these results, a chemoenzymatic synthesis of (S)-5b was developed by using biocatalytic asymmetric reduction as a key step, giving the product with a total yield of 34.0% and 99.9% ee.
- Ou-Yang, Jingping,Zhang, Wenhe,Qin, Fengyu,Zuo, Weiguo,Xu, Shaoyu,Wang, Yan,Qin, Bin,You, Song,Jia, Xian
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- Three-chain truxene discotic liquid crystal showing high charged carrier mobility
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A new truxene discotic liquid crystal possessing only three octyloxy chains (3C8OTRX) was studied on the mesomorphic and semiconducting properties to reveal that it exhibits a high drift mobility of positive carriers in the order of 10-2 cm2 V-1 s-1 in the hexagonal ordered columnar (Colho) mesophase.
- Zhao, Ke-Qing,Chen, Chao,Monobe, Hirosato,Hu, Ping,Wang, Bin-Qin,Shimizu, Yo
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- Design, Synthesis, and Evaluation of Donepezil-Like Compounds as AChE and BACE-1 Inhibitors
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An ecofriendly synthetic pathway for the synthesis of donepezil precursors is described. Alternative energy sources were used for the total synthesis in order to improve yields, regioselectively, and rate of each synthetic step and to reduce the coproduction of waste at the same time. For all products, characterized by an improved structural rigidity respect to donepezil, the inhibitor activity on AChE, the selectivity vs BuChE, the side-activity on BACE-1, and the effect on SHSY-5Y neuroblastoma cells viability were tested. Two potential new lead compounds for a dual therapeutic strategy against Alzheimers disease were envisaged.
- Costanzo, Paola,Cariati, Luca,Desiderio, Doriana,Sgammato, Roberta,Lamberti, Anna,Arcone, Rosaria,Salerno, Raffaele,Nardi, Monica,Masullo, Mariorosario,Oliverio, Manuela
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- Synthesis of 1-indanones by intramolecular Friedel-Crafts reaction of 3-arylpropionic acids catalyzed by Tb(OTf)3
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Intramolecular Friedel-Crafts acylation reaction of 3-arylpropionic acids was efficiently catalyzed by Tb(OTf)3 at 250°C to give 1-indanones. Even deactivated 3-arylpropionic acids with halogen atoms on the aromatic ring can be cyclized in moderation to good yields.
- Cui, Dong-Mei,Zhang, Chen,Kawamura, Masato,Shimada, Shigeru
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- A concise synthesis of 2-benzoyl-1-indanones and 1-indanones from 2-aryl-1-tetralones
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Methyl-2-(3-oxo-3-aryl) benzoates derived from acid catalyzed air oxidative fragmentation of 2-aryl-1-tetralones were efficiently undergone intramolecular-Claisen condensation in the presence of potassium tertiary butoxide. The resulting 2-benzoyl-1-indanones formed in two-step ring contractions were further subjected to indium triflate mediated retro-Claisen condensation to get 1-indanones.
- Kumari, Anusueya,Singh, Saurabh Kumar,Singh, Raj Bahadur,Bhunia, Sabyasachi,Ghosh, Partha
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- Synthesis and biological evaluation of pyridine-linked indanone derivatives: Potential agents for inflammatory bowel disease
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A series of pyridine-linked indanone derivatives were designed and synthesized to discover new small molecules for the treatment of inflammatory bowel disease (IBD). Compounds 5b and 5d exhibited strongest inhibitory activity against TNF-α-induced monocyte adhesion to colon epithelial cells (an in vitro model of colitis). In TNBS (2,4,6-trinitrobenzenesulfonic acid)-induced rat colitis model, oral administration of the compounds 5b and 5d ameliorated colitis with significant recovery in altered expressions of E-cadherin, TNF-α and IL-1β expressions, indicating 5b and 5d as potential agents for therapeutics development against IBD.
- Kadayat, Tara Man,Banskota, Suhrid,Bist, Ganesh,Gurung, Pallavi,Magar, Til Bahadur Thapa,Shrestha, Aarajana,Kim, Jung-Ae,Lee, Eung-Seok
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- Effect of ring size on photoisomerization properties of stiff stilbene macrocycles
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A series of stiff stilbene macrocycles have been studied to investigate the possible impact of the macrocycle ring size on their photodynamic properties. The results show that reducing the ring size counteracts the photoisomerization ability of the macrocycles. However, even the smallest macrocycle studied (stiff stilbene subunits linked by a six carbon chain) showed some degree of isomerization when irradiated. DFT calculations of the energy differences between the E- and Z-isomers show the same trend as the experimental results. Interestingly the DFT study highlights that the energy difference between the E- and Z-isomers of even the largest macrocycle (linked by a twelve carbon chain) is significantly higher than that of the stiff stilbene unit itself. In general, it is indicated that addition of even a flexible chain to the stiff stilbene unit may significantly affect its photochemical properties and increase the photostability of the resulting macrocycle.
- Olsson, Sandra,Pérez, óscar Benito,Blom, Magnus,Gogoll, Adolf
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- Bipolar carrier transport in Tri-Substituted octyloxy-Truxene DLC
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In this study, bipolar charge carrier transport of 2,7,12- trioctyloxytruxene has been studied by a time-of-flight method. The substance studied exhibits a hexagonal columnar mesophase of which melting and clearing points are 118C and 133C, respectively. Ambipolar electronic carrier transports were observed in the mesophase. The drift mobility measurements reveal it is in the order of 10-2cm2 V-1 s-1 in the Colh and it increases to 10-1cm2 V-1 s-1 at the columnar mesophase - metastable phase transition, indicating truxene is an interesting molecular core for mesophase semiconductors. Copyright Taylor & Francis Group, LLC.
- Monobe,Chen,Zhao,Hu,Miyake,Fujii,Ozaki,Shimizu
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- Non-conventional methodologies in the synthesis of 1-indanones
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1-Indanones have been successfully prepared by means of three different non-conventional techniques, namely microwaves, high-intensity ultrasound and a Q-tube reactor. A library of differently substituted 1-indanones has been prepared via one-pot intramolecular Friedel-Crafts acylation and their efficiency and "greenness" have been compared.
- Oliverio, Manuela,Nardi, Monica,Costanzo, Paola,Cariati, Luca,Cravotto, Giancarlo,Giofre, Salvatore Vincenzo,Procopio, Antonio
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- Kinetics-Driven Drug Design Strategy for Next-Generation Acetylcholinesterase Inhibitors to Clinical Candidate
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The acetylcholinesterase (AChE) inhibitors remain key therapeutic drugs for the treatment of Alzheimer's disease (AD). However, the low-safety window limits their maximum therapeutic benefits. Here, a novel kinetics-driven drug design strategy was employed to discover new-generation AChE inhibitors that possess a longer drug-target residence time and exhibit a larger safety window. After detailed investigations, compound 12 was identified as a highly potent, highly selective, orally bioavailable, and brain preferentially distributed AChE inhibitor. Moreover, it significantly ameliorated cognitive impairments in different mouse models with a lower effective dose than donepezil. The X-ray structure of the cocrystal complex provided a precise binding mode between 12 and AChE. Besides, the data from the phase I trials demonstrated that 12 had good safety, tolerance, and pharmacokinetic profiles at all preset doses in healthy volunteers, providing a solid basis for its further investigation in phase II trials for the treatment of AD.
- Zhou, Yu,Fu, Yan,Yin, Wanchao,Li, Jian,Wang, Wei,Bai, Fang,Xu, Shengtao,Gong, Qi,Peng, Tao,Hong, Yu,Zhang, Dong,Zhang, Dan,Liu, Qiufeng,Xu, Yechun,Xu, H. Eric,Zhang, Haiyan,Jiang, Hualiang,Liu, Hong
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p. 1844 - 1855
(2021/03/01)
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- A metal-free method for the facile synthesis of indanonesviathe intramolecular hydroacylation of 2-vinylbenzaldehyde
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A facile method for the synthesis of indanones was developed under metal- and additive-free conditions, whereinl-proline served as an efficient and environmentally benign catalyst. Compared with previously synthesized indanones, synthesis by the transition-metal-catalyzed intramolecular hydroacylation of 2-vinylbenzaldehyde provided a more green synthetic pathway to indanone scaffolds with good to excellent yields. More importantly, it could be used to synthsize the anti-AD drug donepezil.
- He, Guoxue,Ma, Jinyu,Zhou, Jianhui,Li, Chunpu,Liu, Hong,Zhou, Yu
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supporting information
p. 1036 - 1040
(2021/02/09)
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- Iridium Complexes as Efficient Catalysts for Construction of α-Substituted Ketones via Hydrogen Borrowing of Alcohols in Water
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Ketones are of great importance in synthesis, biology, and pharmaceuticals. This paper reports an iridium complexes-catalyzed cross-coupling of alcohols via hydrogen borrowing, affording a series of α-alkylated ketones in high yield (86 %–95 %) and chemoselectivities (>99 : 1). This methodology has the advantages of low catalyst loading (0.1 mol%) and environmentally benign water as the solvent. Studies have shown the amount of base has a great impact on chemoselectivities. Meanwhile, deuteration experiments show water plays an important role in accelerating the reduction of the unsaturated ketones intermediates. Remarkably, a gram-scale experiment demonstrates this methodology of iridium-catalyzed cross-coupling of alcohols has potential application in the practical synthesis of α-alkylated ketones.
- Luo, Nianhua,Zhong, Yuhong,Wen, Huiling,Shui, Hongling,Luo, Renshi
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p. 1355 - 1364
(2021/03/03)
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- Silylative Kinetic Resolution of Racemic 1-Indanol Derivatives Catalyzed by Chiral Guanidine
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Efficient kinetic resolution of racemic 1-indanol derivatives was achieved using triphenylchlorosilane by asymmetric silylation in the presence of chiral guanidine catalysts. The chiral guanidine catalyst (R,R)-N-(1-(β-naphthyl)ethyl)benzoguanidine was found to be highly efficient as only 0.5 mol % catalyst loading was sufficient to catalyze the reaction of various substrates with appropriate conversion and high s-values (up to 89). This catalyst system was successfully applied to the gram-scale silylative kinetic resolution of racemic 1-indanol with high selectivity.
- Yoshimatsu, Shuhei,Yamada, Akira,Nakata, Kenya
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p. 452 - 458
(2018/02/19)
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- AROMATIC KETONE SYNTHESIS WITH AMIDE REAGENTS AND RELATED REACTIONS
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A method of preparing an aryl carbonyl or aryl thiocarbonyl compound, comprises reacting an N-(nitroaryl)-amide or N-(nitroaryl)-thioamide with an aromatic ring, with a superacid catalyst, to produce the aryl carbonyl or aryl thiocarbonyl compound. The superacid is present in an amount of at most 8 equivalents in proportion to the N-(nitroaryl)-amide or N-(nitroaryl)-thioamide. A method of preparing aryl amide or aryl thioamide, comprises reacting an N-(nitroaryl)-carbamide or N-(nitroaryl)-thiocarbamide with an aromatic ring, with a superacid catalyst, to produce the aryl amide or aryl thioamide.
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Paragraph 0038-0039
(2013/10/22)
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- Friedel-crafts acylation with amides
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Friedel-Crafts acylation has been known since the 1870s, and it is an important organic synthetic reaction leading to aromatic ketone products. Friedel-Crafts acylation is usually performed with carboxylic acid chlorides or anhydrides, while amides are generally not useful substrates in these reactions. Despite being the least reactive carboxylic acid derivative, we have found a series of amides capable of providing aromatic ketones in good yields (55-96%, 17 examples). We propose a mechanism involving diminished C-N resonance through superelectrophilic activation and subsequent cleavage to acyl cations.
- Raja, Erum K.,Deschepper, Daniel J.,Nilsson Lill, Sten O.,Klumpp, Douglas A.
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p. 5788 - 5793
(2012/07/30)
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- Synthesis and evaluation of dimeric 1,2,3,4-Tetrahydro-naphthalenylamine and Indan-1-ylamine derivatives with mast cell-stabilising and anti-allergic activity
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In a continuation of our studies into 4-Amino-3,4-dihydro-2H-naphthalen-1-ones as novel modulators of allergic and inflammatory phenomena, we have extended our work to include dimeric analogues. Of these derivatives, the most promising activity was seen with tertiary amine 58a, which exhibited potent mast cell-stabilising activity in vitro against a variety of stimuli and also in vivo against passive cutaneous anaphylaxis.
- Barlow, James W.,Walsh, John J.
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scheme or table
p. 25 - 37
(2010/03/04)
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- A study on the conversion of indanones into carbostyrils
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We have surveyed the utility of Beckmann rearrangement for the conversion of indanones into carbostyrils. Initial attempts at the conversion of 6-methoxy indanone oxime under classical conditions resulted in the formation of the two unusual products: 2-sulfonyloxyindanone and the dimeric product. This unusual rearrangement was also observed by the treatment of some metal triflates species. Further investigation has led to the development of reliable conditions starting from oxime mesylate (not oxime tosylate), in which some strong Lewis acid catalyst (ZrCl4) was employed in either a conventional or non-conventional solvent system. The advantage of the new protocol is highlighted by the simple work up and direct isolation of the product in 65% isolated yield.
- Torisawa, Yasuhiro,Nishi, Takao,Minamikawa, Jun-Ichi
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p. 2205 - 2209
(2007/10/03)
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- Oxidative kinetic resolution of racemic alcohols catalyzed by chiral ferrocenyloxazolinylphosphine - Ruthenium complexes
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Oxidative kinetic resolution of racemic secondary alcohols by using acetone as a hydrogen acceptor in the presence of a catalytic amount of [RuCl2(PPh3)(ferrocenyloxazolinylphosphine)] (2) proceeds effectively to recover the corresponding alcohols in high yields with an excellent enantioselectivity. When 1-indanol is employed as a racemic alcohol, the oxidation proceeds quite smoothly even in the presence of 0.0025 mol % of the catalyst 2 to give an optically active 1-indanol in good yield with high enantioselectivity (up to 94% ee), where turnover frequency (TOF) exceeds 80 000 h-1. From a practical viewpoint, the kinetic resolution is investigated in a large scale, optically pure (S)-1-indanol (75 g, 56% yield, > 99% ee) being obtained from racemic 1-indanol (134 g) by employing this kinetic resolution method twice.
- Nishibayashi, Yoshiaki,Yamauchi, Akiyoshi,Onodera, Gen,Uemura, Sakae
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p. 5875 - 5880
(2007/10/03)
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- Low temperature, high conversion, liquid-phase benzylic oxidation with dioxygen by metal/NHPI-catalyzed co-oxidation with benzaldehyde
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A new liquid-phase catalytic oxidation system for the low temperature, high conversion benzylic mono-oxyfunctionalization of 10,11-dihydrocarbamazepine (1) into oxcarbazepine (4) with dioxygen has been developed. The method is based on a co-oxidation of 1 with benzaldehyde in the presence of a four-component catalyst system consisting of Co(OAc)2, Ni(OAc)2, Cr(NO3)3, and N-hydroxyphthalimide (NHPI). The influence of the catalyst system on the formation and decomposition of the crucial hydroperoxide intermediate 2 has been investigated. Based on these results, the role of each of the components in the catalyst system is discussed. The scope of this method for the oxidation of other substrates has been studied, and the results are compared with those obtained by Co/NHPI catalyzed oxidation of these substrates. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
- De Vondervoort, Lizette Schmieder-van,Bouttemy, Sabine,Heu, Ferdinand,Weissenboeck, Kurt,Alsters, Paul L.
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p. 578 - 586
(2007/10/03)
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- Interesting reaction of the indanone oximes under Beckmann rearrangement conditions
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Attempted Beckmann rearrangement of the 6-methoxyindanone oximes in conventional conditions resulted in the formation of the two kinds of unexpected products: 2-sulfonyloxyindanone and the dimeric product. Related rearrangement was also observed in the re
- Torisawa, Yasuhiro,Nishi, Takao,Minamikawa, Jun-Ichi
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p. 387 - 390
(2007/10/03)
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- Synthesis and Na+/H+ exchange inhibitory activity of indanylideneacetylguanidines
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Synthesis of indanylideneacetylguadines 7a-i and their corresponding reduced compounds 8a-e has been achieved and their Na+/H+ exchange inhibitory activity evaluated. All the compounds studied exhibit significant inhibition of Na+/H+ exchanger activity. Promising activity is shown by compounds 7g, 8b and 8d. From the structure activity analysis, it appears that reduction of exocyclic double bond is associated with a marked increase in inhibitory activity.
- Ramakrishna,Jain,Ghate,Gupte,Vadlamudi
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p. 407 - 412
(2007/10/03)
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- Selective oxidation of benzylic hydrocarbons to carbonyl compounds catalyzed by Mn(III) salen complexes
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Selective oxidation of benzylic hydrocarbons to the carbonyl compounds was achieved using a racemic Mn(III) salen complex 1 as the catalyst. The reaction proceeds in good yields under mild reaction conditions using iodosobenzene or aq. sodium hypochlorite as a stoichiometric oxidant.
- Lee, Nam Ho,Lee, Chang-Seob,Jung, Duk-Sang
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p. 1385 - 1388
(2007/10/03)
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- Heterogeneous Permanganate Oxidations. 7. the Oxidation of Aliphatic Side Chains
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Alkylbenzene side chains are oxidized at the benzylic position when treated under heterogeneous conditions with permanganate adsorbed on a solid support. The products are alcohols if the benzylic carbon is tertiary, or ketones if it is secondary. Carbon-carbon bond cleavage, which usually occurs when these same compounds are oxidized by permanganate under homogeneous conditions, does not occur. A unique selectivity is observed for the oxidation of derivatives of indane, 1, and tetralin, 2, in which one of the methylenes is replaced by an oxygen. If the oxygen is in the α-position, no reaction occurs; if it is in the β-position, good yields of the corresponding lactone are obtained. A mechanism consistent with the observed selectivity has been proposed.
- Noureldin, Nazih A.,Zhao, Dongyuan,Lee, Donald G.
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p. 8767 - 8772
(2007/10/03)
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- Substituted heterocyclylisoquinolinium salts and compositions and method of use thereof
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Substitutued heterocyclylisoquinolinium salts, pharmaceutical compositions containing them and methods for the treatment or prevention of neurodegenerative disorders or neurotoxic injuries utilizing them.
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- Substituted 6,11-ethano-6,11-dihydrobenzo[b] quinolizinium salts and compositions and methods of use thereof
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Substituted 6,11-ethano-6,11-dihydrobenzo[b]quinolizinium salts, pharmaceutical compositions containing them, and methods for the treatment of neurodegenerative disorders or neurotoxic injuries utilizing them, wherein the substituted 6,11-ethano-6,11-dihydrobenzo[b]quinolizinium salts have the formula: STR1 wherein: R1, R2, R3, R4, R5, R6, R7, X and p are as defined in the specification.
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- Heterogeneous permanganate oxidations; part 6: Selective oxidation of arenes
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Potassium permanganate adsorbed on alumina selectively oxidizes arenes at the benzylic position. If the benzyl carbon is secondary, ketones are obtained in good yields; alcohols are produced if the benzylic position is tertiary. Benzopyranoid and benzofuranoid systems exhibit highly selective oxidation patterns. Decarboxylation occurs when phenylacetic acid is oxidized, but not when the corresponding ester, ethyl phenylacetate, is oxidized to ethyl benzoylformate.
- Zhao,Lee
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p. 915 - 916
(2007/10/02)
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- Rhodium Complex-Catalyzed Desilylative Cyclocarbonylation of 1-Aryl-2-(trimethylsilyl)acetylenes: A New Route to 2,3-Dihydro-1H-inden-1-ones
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Under water gas shift reaction conditions, 1-aryl-2-(trimethylsilyl)acetylenes undergo Rh-catalyzed desilylative cyclocarbonylation to give 2,3-dihydro-1H-inden-1-ones and trimethylsilanol.A wide variety of functional groups, such as methoxy, chloro, acetyl, ethoxycarbonyl, cyano, and trifluoromethyl, are tolerated on the aromatic ring under the reaction conditions.The products were obtained in good to excellent yield whether the substituent on the aromatic ring was electron-donating or electron-withdrawing.The cyclizations of substrates bearing a meta substituent onthe aromatic ring regiospecifically gave 5-substituted-2,3-dihydro-1H-inden-1-ones except when the meta substituent was a methoxy group.The desilylative cyclocarbonylation is an alternative to the conventional preparation of 2,3-dihydro-1H-inden-1-ones, an intramolecular Friedel-Crafts acylation.A possible mechanism for the process is described.
- Takeuchi, Ryo,Yasue, Hiroyuki
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p. 5386 - 5392
(2007/10/02)
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- An unusual C-C bond cleavage with chromium VI reagents: Oxidation of primary alcohols to ketones
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Oxidation of 1-hydroxymethylindanes and 1-hydroxymethyltetralins with PDC or PCC in methylene chloride affords 1-indanones and 1-tetralones.
- Bijoy,Subba Rao
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p. 2701 - 2708
(2007/10/02)
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- Polyphosphoric Acid Catalyzed Conversion of 3-(Methoxyphenyl)propionic Acids to Derivatives of Metacyclophane-1,10-diones and 1-Indanones
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Polyphosphoric acid (PPA) catalyzed cycliacylation of 3-(2-methoxy- and 2,4-dimethoxyphenyl)propionic acids (1a,b) results in dimeric products: 46 and 49percent yields of 5,14-dimethoxy- and 5,7,14,16-tetramethoxymetacyclophane-1,10-diones (5a,b) and
- Zhang, Juan,Hertzler, Russell L.,Holt, Elizabeth M.,Vickstrom, Thayne,Eisenbraun, Edmund J.
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p. 556 - 559
(2007/10/02)
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- Synthetic routes to ninhydrins. Preparation of ninhydrin, 5-methoxyninhydrin, and 5-(methylthio)ninhydrin
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Two syntheses of 5-methoxyninhydrin (2,2-dihydroxy-5-methoxy-1,3-indanedione) are described. One method employs a novel and efficient two step route, which begins with commercially available 6-methoxy-1-indanone. The application of this strategy for the preparation of a new ninhydrin derivative, 5-(methylthio)ninhydrin, and ninhydrin is also presented.
- Heffner,Joullie
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p. 2231 - 2256
(2007/10/02)
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- The effects of solvent and temperature on the orientation of cycloaddition reaction of 1,2,3-triazine with enamines: Its application to the synthesis of alkaloids, onychine and 6-methoxyonychine
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4-Methyl-1,2,3-triazine was treated with several enamines in chloroform to afford 2,5,6-trisubstituted pyridines. In each case, cycloaddition occurs N-3 C-6 of the 1,2,3-triazine nucleus. On the other hand, when high boiling solvent was employed, cycloaddition took place involving the N-3 C-6 cycloadduct and N-1 C-4 cycloadduct. As application of synthetic method, we accomplished the synthesis of alkaloids, onychine and 6-methoxyonychine.
- Okatani, Teruyo,Koyama, Junko,Suzuta, Yukio,Tagahara, Kiyoshi
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p. 2213 - 2217
(2007/10/02)
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- Substituent Effect in Solvolysis of Spiro-1'-yl p-Nitrobenzoate
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The preparation of a series of substituted spiro-1'-yl p-nitrobenzoates (4a-g) is described.The solvolysis rate constant is k = 8.53 * 10-5 s-1 at 25 deg C in 80percent aqueous acetone for the unsaturated derivative (4e) and is relatively high in comparison with the related secondary systems.The Hammett treatment (ρ?+) gives a straight line and the ρ value (-3.33) is more negative than that (-2.11) of 3,4-benzotricyclo1,6>-dec-3-en-2-anti-yl p-nitrobenzoate (1).On the basis of the results, it can be considered that the mesomeric transmission of substituent effect is very weak in 1 relative to 4.
- Ohkata, Katsuo,Akiyama, Masaki,Wada, Kenshi,Sakaue, Shun,Toda, Yoshiko,Hanafusa, Terukiyo
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p. 2517 - 2520
(2007/10/02)
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- Synthesis of Substituted Indans as Prostacyclin Analogues
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A route is described to the substituted indans (8) and (10), prepared as analogues of prostaglandin I2 (prostacyclin).Two key steps in the synthesis involve the regiospecific attack of lithium salts from allylic sulphides onto indene oxides and, after oxidation to the corresponding sulphoxides, their reductive rearrangement to the required diols.Using model indene oxides, attempts have been made to direct the stereochemistry of the exocyclic hydroxy group by steric control during formation of the precursor sulphide.
- Phialas, Memnon,Sammes, Peter G.,Kennewell, Peter D.,Westwood, Robert
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p. 687 - 695
(2007/10/02)
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- 3-NITROCYCLOALKENONES, SYNTHESIS AND USE AS REVERSE AFFINITY CYCLOALKYNONE EQUIVALENTS
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A partical synthesis of 3-nitrocycloalkenones and their utilization as dienophiles in the Diels-Alder reaction are discribed.The results demonstrate a reverse affinity equivalency between these β-nitro-enones and "cycloalkynones".
- Corey, E. J.,Estreicher, Herbert
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p. 603 - 606
(2007/10/02)
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