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Aluminum Metal-Organic Framework-Ligated Single-Site Nickel(II)-Hydride for Heterogeneous Chemoselective Catalysis
The development of chemoselective and heterogeneous earth-abundant metal catalysts is essential for environmentally friendly chemical synthesis. We report a highly efficient, chemoselective, and reusable single-site nickel(II) hydride catalyst based on robust and porous aluminum metal-organic frameworks (MOFs) (DUT-5) for hydrogenation of nitro and nitrile compounds to the corresponding amines and hydrogenolysis of aryl ethers under mild conditions. The nickel-hydride catalyst was prepared by the metalation of aluminum hydroxide secondary building units (SBUs) of DUT-5 having the formula of Al(μ2-OH)(bpdc) (bpdc = 4,4′-biphenyldicarboxylate) with NiBr2 followed by a reaction with NaEt3BH. DUT-5-NiH has a broad substrate scope with excellent functional group tolerance in the hydrogenation of aromatic and aliphatic nitro and nitrile compounds under 1 bar H2 and could be recycled and reused at least 10 times. By changing the reaction conditions of the hydrogenation of nitriles, symmetric or unsymmetric secondary amines were also afforded selectively. The experimental and computational studies suggested reversible nitrile coordination to nickel followed by 1,2-insertion of coordinated nitrile into the nickel-hydride bond occurring in the turnover-limiting step. In addition, DUT-5-NiH is also an active catalyst for chemoselective hydrogenolysis of carbon-oxygen bonds in aryl ethers to afford hydrocarbons under atmospheric hydrogen in the absence of any base, which is important for the generation of fuels from biomass. This work highlights the potential of MOF-based single-site earth-abundant metal catalysts for practical and eco-friendly production of chemical feedstocks and biofuels.
Antil, Neha,Kumar, Ajay,Akhtar, Naved,Newar, Rajashree,Begum, Wahida,Dwivedi, Ashutosh,Manna, Kuntal
p. 3943 - 3957
(2021/04/12)

Method for preparing lorcaserin
The invention discloses a method for preparing lorcaserin. Specifically, the method comprises the steps: taking p-chlorophenylacetonitrile as an initial raw material, preparing p-chlorophenylethylamine through reduction; carrying out a reaction with p-toluenesulfonyl chloride to form an amino occupying intermediate; enabling the intermediate to carry out a reaction with monochloroacetone under analkaline condition to form N-(2-(4-chlorphenyl)ethyl)-4-methyl-N-(2-propionyl)benzenesulfonamide, and then carrying out reduction, chlorination, p-toluenesulfonyl removal and intramolecular Friedel-Crafts alkylation to synthesize 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzoazepine, carrying out L-(+)-tartaric acid resolution and alkalization on azepine to remove tartaric acid, and acting with hydrogen chloride diethyl ether to salify to prepare lorcaserin. The method has the characteristics of simple synthesis method, good reaction selectivity, high product purity, environmental protectionand low preparation cost.
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Paragraph 0009-0011

(2020/08/22)

Bi-enzymatic Conversion of Cinnamic Acids to 2-Arylethylamines
The conversion of carboxylic acids, such as acrylic acids, to amines is a transformation that remains challenging in synthetic organic chemistry. Despite the ubiquity of similar moieties in natural metabolic pathways, biocatalytic routes seem to have been overlooked for this purpose. Herein we present the conception and optimisation of a two-enzyme system, allowing the synthesis of β-phenylethylamine derivatives from readily-available ring-substituted cinnamic acids. After characterisation of both parts of the reaction in a two-step approach, a set of conditions allowing the one-pot biotransformation was optimised. This combination of a reversible deaminating and irreversible decarboxylating enzyme, both specific for the amino acid intermediate in tandem, represents a general method by which new strategies for the conversion of carboxylic acids to amines could be designed.
Weise, Nicholas J.,Thapa, Prasansa,Ahmed, Syed T.,Heath, Rachel S.,Parmeggiani, Fabio,Turner, Nicholas J.,Flitsch, Sabine L.
p. 995 - 998
(2020/01/21)

Enantioselective Sequential-Flow Synthesis of Baclofen Precursor via Asymmetric 1,4-Addition and Chemoselective Hydrogenation on Platinum/Carbon/Calcium Phosphate Composites
Continuous-flow synthesis of baclofen precursor (2) was achieved using achiral and chiral heterogeneous catalysts in high yield with high enantioselectivity. The key steps are chiral calcium-catalyzed asymmetric 1,4-addition of a malonate to a nitroalkene and chemoselective reduction of a nitro compound to the corresponding amino compound by using molecular hydrogen. A dimethylpolysilane (DMPS)-modified platinum catalyst supported on activated carbon (AC) and calcium phosphate (CP) has been developed that has remarkable activity for the selective hydrogenation of nitro compounds.
Furiya, Yuichi,Ishitani, Haruro,Kobayashi, Shu
supporting information

(2020/05/05)

Old Concepts, New Application – Additive-Free Hydrogenation of Nitriles Catalyzed by an Air Stable Alkyl Mn(I) Complex
An efficient additive-free manganese-catalyzed hydrogenation of nitriles to primary amines with molecular hydrogen is described. The pre-catalyst, a well-defined bench-stable alkyl bisphosphine Mn(I) complex fac-[Mn(dpre)(CO)3(CH3)] (dpre=1,2-bis(di-n-propylphosphino)ethane), undergoes CO migratory insertion into the manganese-alkyl bond to form acyl complexes which upon hydrogenolysis yields the active coordinatively unsaturated Mn(I) hydride catalyst [Mn(dpre)(CO)2(H)]. A range of aromatic and aliphatic nitriles were efficiently and selectively converted into primary amines in good to excellent yields. The hydrogenation of nitriles proceeds at 100 °C with a catalyst loading of 2 mol % and a hydrogen pressure of 50 bar. Mechanistic insights are provided by means of DFT calculations. (Figure presented.).
Weber, Stefan,Veiros, Luis F.,Kirchner, Karl
p. 5412 - 5420
(2019/11/13)

Combined Photoredox/Enzymatic C?H Benzylic Hydroxylations
Chemical transformations that install heteroatoms into C?H bonds are of significant interest because they streamline the construction of value-added small molecules. Direct C?H oxyfunctionalization, or the one step conversion of a C?H bond to a C?O bond, could be a highly enabling transformation due to the prevalence of the resulting enantioenriched alcohols in pharmaceuticals and natural products,. Here we report a single-flask photoredox/enzymatic process for direct C?H hydroxylation that proceeds with broad reactivity, chemoselectivity and enantioselectivity. This unified strategy advances general photoredox and enzymatic catalysis synergy and enables chemoenzymatic processes for powerful and selective oxidative transformations.
Betori, Rick C.,May, Catherine M.,Scheidt, Karl A.
supporting information
p. 16490 - 16494
(2019/11/03)

Method for synthesizing lorcaserin intermediate p-chlorophenethylamine
The invention discloses a method for synthesizing a lorcaserin intermediate, namely p-chlorophenethylamine. The method is characterized in that p-chlorophenethylamine is prepared from p-halogen chlorobenzene and halogenated ethylamine under the action of a catalyst, and the reaction process comprises the following steps: 1) uniformly mixing halogenated ethylamine, a protecting agent, an alkali 1 and a solvent S1, stirring at 50-70 DEG C to perform a reaction for 6-8h, and filtering off solids so as to obtain a mixture M1; 2) under the protection of a protection gas, uniformly mixing p-halogenchlorobenzene, copper iodide, a solid alkali and a solvent S2, controlling a reaction temperature to 130-145 DEG C and reaction pressure to 3-5atm, stirring for 50-70min, dropping the mixture M1, controlling the reaction temperature to 150-170 DEG C and the reaction pressure to 5-7atm after dropping is completed, and carrying out a reaction for 1-2 so as to obtain a mixture M2; 3) putting a hydrochloric acid solution into the mixture M2, controlling the reaction temperature to 80-90 DEG C and t he reaction pressure to 2-3atm, and carrying out a reaction for 40-60min so as to obtain a mixture M3; and 4) putting an alkali 2 into the mixture M3 to adjust the pH value to 4, controlling the temperature to be less than 70 DEG C, cooling, leaving to stand and layer, washing an organic phase withwater, drying with a drying agent, and concentrating and evaporating off the solvents, thereby obtaining a product. The method is simple in operation, and no toxic substance is used.
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Paragraph 0031; 0037-0039; 0040; 0046-0048; 0049; 0055-0057

(2019/09/13)

Ruthenium(II)-cored supramolecular organic framework-mediated recyclable visible light photoreduction of azides to amines and cascade formation of lactams
Ru(bpy)3]2+-cored supramolecular organic framework SMOF-1, assembled from a [Ru(bpy)3]2+-derived hexaarmed molecule and cucurbit[8]uril, has been demonstrated to heterogeneously catalyze visible light-induced reduction of phenyl, benzyl, 2-phenylethyl and 3-phenylpropyl azides in acetonitrile to produce the corresponding amines in good to high yields. For the last two kinds of azides that bear a CO2Me group at the para-position of the benzene ring, cascade reactions take place to generate the corresponding lactams in high yields. Compared with homogeneous control [Ru(bpy)3]Cl2, SMOF-1 exhibits remarkably increased photocatalysis activity as a result of synergistic effect of the [Ru(bpy)3]2+ units that form cubic cages to host the azide molecules and related intermediates. Moreover, SMOF-1 displays high recyclability and considerable photocatalysis activity after 3 to 12 runs.
Wu, Yi-Peng,Yan, Meng,Gao, Zhong-Zheng,Hou, Jun-Li,Wang, Hui,Zhang, Dan-Wei,Zhang, Junliang,Li, Zhan-Ting
p. 1383 - 1386
(2019/05/06)

Deacetylative Amination of Acetyl Arenes and Alkanes with C-C Bond Cleavage
The Br?nsted acid-catalyzed synthesis of primary amines from acetyl arenes and alkanes with C-C bond cleavage is described. Although the conversion from an acetyl group to amine has traditionally required multiple steps, the method described herein, which uses an oxime reagent as an amino group source, achieves the transformation directly via domino transoximation/Beckmann rearrangement/Pinner reaction. The method was also applied to the synthesis of γ-aminobutyric acids, such as baclophen and rolipram.
Hyodo, Kengo,Hasegawa, Genna,Maki, Hiroya,Uchida, Kingo
supporting information
p. 2818 - 2822
(2019/04/25)

Preparation method of lorcaserin intermediate
The invention discloses a preparation method of a lorcaserin intermediate (I). According to the preparation method, p-chlorobenzyl cyanide is taken as the primary raw material, and the lorcaserin intermediate (I) is obtained after reduction reactions and condensation reactions. The primary raw materials (p-chlorobenzyl cyanide and 1-chloro-2-propanol) are cheap and easily available; raw materials, which can easily get polluted and are explosive, such as sulfoxide chloride, hydrobromic acid, borane, and the like are not used; the preparation method will not produce a large amount of wastewater and is beneficial for the environment protection; moreover, the requirements on the protection of workers are lowered, and safe production is guaranteed. The route design is novel, the raw materials are easily available, the operation is simple and feasible, and the preparation method is environment-friendly and can be applied to massive industrial production.
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Paragraph 0019; 0020

(2017/08/29)

Reduction of selenoamides to amines using SmI2-H2O
Selenoamides are selectively reduced to amines by SmI2 with H2O. The process is general for primary, secondary, and tertiary aryl and alkyl selenoamide substrates and selectively delivers amine products. The reduction proceeds under mild conditions using SmI2 activated by straightforward addition of H2O, and does not require an additional Lewis base additive.
Thurow, Samuel,Lenardo, Eder J.,Just-Baringo, Xavier,Procter, David J.
p. 50 - 53
(2017/11/28)

Bifunctional N-Doped Co@C Catalysts for Base-Free Transfer Hydrogenations of Nitriles: Controllable Selectivity to Primary Amines vs Imines
The transfer hydrogenation of nitriles is an important and alternative strategy to produce primary amines or imines, both of which play a crucial role in the synthesis of fine chemicals and pharmaceuticals. Nevertheless, developing highly active bifunctional catalyst system with controllable selectivity for these reactions still remains a huge challenge. In this study, we presented a bifunctional N-doped Co@C catalyst system (Co@NC) for the selective transfer hydrogenation of nitriles into either primary amines or imines. The Co@NC was prepared by the direct pyrolysis of an N-containing Co-MOF under an inert atmosphere, where the N-containing ligands could be transformed into highly graphitic N-doped carbon, endowing the catalysts with high-density special basic sites, while the Co2+ ions were reduced to uniform Co nanoparticles which were dispersed on or embedded in N-doped graphitic structures. Under base-free conditions with isopropyl alcohol as both proton donor and solvent, the optimized Co@NC-900 (obtained at 900 °C) catalyst could convert nitriles into primary amines or imines at will with surprising selectivities (mostly higher than 90%), depending on the solvent volume added to the reaction systems. Furthermore, a possible reaction mechanism was proposed. The N-derived basic sites on Co@NC could play a role similar to that of the base additives, which not only inhibit the formation of polyamine or prevent the products stacked on the surface of catalysts but also effectively promote the transfer hydrogenation of nitriles. The generated corresponding primary imines could controllably attack the primary imine intermediates to form imines by adjusting the concentration of Co@NC. It is clear that this strategy offers a high-performance catalyst system for base-free transfer hydrogenations of nitriles to selectively produce primary amines vs imines.
Long, Jilan,Shen, Kui,Li, Yingwei
p. 275 - 284
(2017/06/07)

Biocatalytic Formal Anti-Markovnikov Hydroamination and Hydration of Aryl Alkenes
Biocatalytic anti-Markovnikov alkene hydroamination and hydration were achieved based on two concepts involving enzyme cascades: epoxidation-isomerization-amination for hydroamination and epoxidation-isomerization-reduction for hydration. An Escherichia coli strain coexpressing styrene monooxygenase (SMO), styrene oxide isomerase (SOI), ω-transaminase (CvTA), and alanine dehydrogenase (AlaDH) catalyzed the hydroamination of 12 aryl alkenes to give the corresponding valuable terminal amines in high conversion (many ≥86%) and exclusive anti-Markovnikov selectivity (>99:1). Another E. coli strain coexpressing SMO, SOI, and phenylacetaldehyde reductase (PAR) catalyzed the hydration of 12 aryl alkenes to the corresponding useful terminal alcohols in high conversion (many ≥80%) and very high anti-Markovnikov selectivity (>99:1). Importantly, SOI was discovered for stereoselective isomerization of a chiral epoxide to a chiral aldehyde, providing some insights on enzymatic epoxide rearrangement. Harnessing this stereoselective rearrangement, highly enantioselective anti-Markovnikov hydroamination and hydration were demonstrated to convert α-methylstyrene to the corresponding (S)-amine and (S)-alcohol in 84-81% conversion with 97-92% ee, respectively. The biocatalytic anti-Markovnikov hydroamination and hydration of alkenes, utilizing cheap and nontoxic chemicals (O2, NH3, and glucose) and cells, provide an environmentally friendly, highly selective, and high-yielding synthesis of terminal amines and alcohols.
Wu, Shuke,Liu, Ji,Li, Zhi
p. 5225 - 5233
(2017/08/17)

Preparation and characterization of primary amines by potassium borohydride-copper chloride system from nitriles
Nitriles undergo reduction to primary amines under optimized conditions at 50 °C using 0.25 equiv of copper chloride and 3.0 equiv of potassium borohydride in 80 % isopropanol. The aromatic and aralkyl nitriles could be effectively reduced in yield ranging from 60 to 90 %.
Jiang, Han,Hu, Jialei,Xu, Xinliang,Zhou, Yifeng
p. 3564 - 3566
(2015/12/30)

Electron transfer reduction of nitriles using SmI2-Et 3N-H2O: Synthetic utility and mechanism
The first general reduction of nitriles to primary amines under single electron transfer conditions is demonstrated using SmI2 (Kagan's reagent) activated with Lewis bases. The reaction features excellent functional group tolerance and represents an attractive alternative to the use of pyrophoric alkali metal hydrides. Notably, the electron transfer from Sm(II) to CN functional groups generates imidoyl-type radicals from bench stable nitrile precursors.
Szostak, Michal,Sautier, Brice,Spain, Malcolm,Procter, David J.
supporting information
p. 1092 - 1095
(2014/03/21)

17a-HYDROXYLASE/C17,20-LYASE INHIBITORS
The present invention provides compounds of Formula (I), or a pharmaceutically acceptable salt thereof, where R1, R2, R3, R4, R5, R6, A and n are as defined herein. A deuteriated derivative of the compound of Formula (I) is also provided.
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Paragraph 0173; 0174

(2014/03/21)

Synthesis and evaluation of N-alkyl-S-[3-(piperidin-1-yl)propyl] isothioureas: High affinity and human/rat species-selective histamine H 3 receptor antagonists
S-Alkyl-N-alkylisothiourea compounds containing various cyclic amines were synthesized in the search for novel nonimidazole histamine H3 receptor (H3R) antagonists. Among them, four N-alkyl S-[3-(piperidin-1-yl)propyl]isothioureas 18, 19, 22, and 23 were found to exhibit potent and selective H3R antagonistic activities against in vitro human H3R, but were inactive against in vitro human H 4R. Furthermore, three alkyl homologs 18-20 showed inactivity for histamine release in in vivo rat brain microdialysis, suggesting differences in antagonist affinities between species. In addition, in silico docking studies of N-[4-(4-chlorophenyl)butyl]-S-[3-piperidin-1-yl)propyl]isothiourea 19 and a shorter homolog 17 with human/rat H3Rs revealed that structural differences between the antagonist-docking cavities of rat and human H 3Rs were likely caused by the Ala122/Val122 mutation.
Harusawa, Shinya,Sawada, Koichi,Magata, Takuji,Yoneyama, Hiroki,Araki, Lisa,Usami, Yoshihide,Hatano, Kouta,Yamamoto, Kouichi,Yamamoto, Daisuke,Yamatodani, Atsushi
p. 6415 - 6420
(2013/11/19)

17α-HYDROXYLASE/C17,20-LYASE INHIBITORS
The present invention provides compounds of Formula (I), or a pharmaceutically acceptable salt thereof, where R1, R2, R3, R4, R5, R6, A and n are as defined herein. A deuteriated derivative of the compound of Formula (I) is also provided.
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Page/Page column 35

(2012/04/04)

Activation of electrophilicity of stable Y-delocalized carbamate cations in intramolecular aromatic substitution reaction: Evidence for formation of diprotonated carbamates leading to generation of isocyanates
Although cations with three heteroatoms, such as monoprotonated guanidine and urea, are stabilized by Y-shaped conjugation and such Y-conjugated cations are sufficiently basic to be further protonated (or protosolvated) to dications in strongly acid media, only O-monoprotonated species have been detected in the case of carbamates even in magic acid. We found that the trifluoromethanesulfonic acid-catalyzed cyclization of arylethylcarbamates proceeds to afford dihydroisoquinolones in high yield. In strong acids, methyl carbamates are fully O-monoprotonated, and these monocations do not undergo cyclization even under heating. But, as the acidity of the reaction medium is further increased, the cyclization reaction of methyl phenethylcarbamates starts to proceed as a first-order reaction, with a linear relationship between rate and acidity. The sign and magnitude of the entropy of activation ΔS ? were found to be similar to those of other AAc1 reactions. These results strongly support the idea that further protonation of the O-protonated carbamates is involved in the cyclization, but the concentration of the dications is very low and suggests that the rate-determining step is dissociation of methanol from the diprotonated carbamate to generate protonated isocyanate, which reacts with the aromatic ring. Therefore, O-protonated carbamates are weak bases in sharp contrast to other Y-shaped monocations.
Kurouchi, Hiroaki,Kawamoto, Kyoko,Sugimoto, Hiromichi,Nakamura, Satoshi,Otani, Yuko,Ohwada, Tomohiko
p. 9313 - 9328,16
(2012/12/11)

Instantaneous deprotection of tosylamides and esters with Sml 2/amine/water
(Chemical Equation Presented) Sml2/amine/water mediates instantaneous cleavage of tosyl amides and tosyl esters. Highly hindered, sensitive and functionalized substrates were successfully deprotected in near quantitative yield.
Ankner, Tobias,Hilmersson, Goeran
supporting information; scheme or table
p. 503 - 506
(2009/07/11)

Instantaneous SmI2/H2O/amine mediated reduction of nitroalkanes and α,β-unsaturated nitroalkenes
A rapid method for efficient reduction of nitroalkanes and α,β-unsaturated nitroalkenes using SmI2/H2O/amine has been developed.
Ankner, Tobias,Hilmersson, G?ran
p. 5707 - 5710
(2008/02/10)

Aromatic chlorination of ω-phenylalkylamines and ω- phenylalkylamides in carbon tetrachloride and α,α,α- trifluorotoluene
The aromatic halogenation of simple alkylbenzenes with chlorine proceeds smoothly in acetic acid but is much less efficient in less polar solvents. By contrast chlorination of ω-phenylalkylamines, such as 3-phenylpropylamine, occurs readily in either acetic acid, carbon tetrachloride or α,α,α-trifluorotoluene, and in the latter solvents gives high proportions of ortho-chlorinated products. These effects are attributable to the involvement of N-chloroamines as reaction intermediates, with intramolecular delivery of the chlorine electrophile. ω-Phenylalkylamides, such as 3-phenylpropionamide, also easily undergo aromatic chlorination in carbon tetrachloride and α,α,α-trifluorotoluene. These reactions generally show a first-order dependence on the substrate concentration, but not on the amount of chlorine. With carbon tetrachloride, very similar reaction rates are observed with chlorine concentrations ranging from 0.1-1.5 M. In α,α,α-trifluorotoluene, the rates reach a plateau at a chlorine concentration of approximately 0.2 M. These features indicate that the reactions proceed via the formation of intermediates which evidence suggests may be the corresponding O-chloroimidates. Irrespective of the mechanistic details, the reactions are remarkably rapid, being faster than analogous reactions in acetic acid and three to four orders of magnitude more rapid than reactions of simple alkylbenzenes in carbon tetrachloride. Therefore, chlorination of the amines and amides may be accomplished without the need for highly polar solvents, added catalysts or large excesses of chlorine, which are often employed for electrophilic aromatic substitutions. Although the use of carbon tetrachloride is becoming increasingly impractical due to environmental concerns, the trifluorotoluene is a suitable alternative. The Royal Society of Chemistry 2006.
O'Connell, Jenny L.,Simpson, Jamie S.,Dumanski, Paul G.,Simpson, Gregory W.,Easton, Christopher J.
p. 2716 - 2723
(2008/02/08)

The influence of substitution at aromatic part of 1,2,3,4-tetrahydroisoquinoline on in vitro and in vivo 5-HT1A/5-HT2A receptor activities of its 1-adamantoyloaminoalkyl derivatives
Further structure-activity relationship (SAR) studies with the 1,2,3,4-tetrahydroisoquinoline (THIQ) class of 5-HT1A ligands led to the synthesis of new 1-adamantoyloaminoalkyl derivatives. The impact of substituent variations in the aromatic part of THIQ moiety on 5-HT1A and 5-HT2A receptor affinities, as well as in vivo functional properties of the investigated compounds were discussed. It was found that modification reduced the binding affinity for 5-HT1A receptors (in comparison with unsubstituted THIQ derivatives); however, the majority of new compounds still remained potent 5-HT1A ligands (Ki = 4.9-46 nM) and most of them showed features of partial agonists of postsynaptic 5-HT1A receptors. At the same time, their 5-HT2A receptor affinity was slightly increased (Ki = 40-1475 nM), which resulted in a loss of 5-HT2A/5-HT1A selectivity. 5-Br,8-OCH3 derivative - the most potent, mixed 5-HT1A/5-HT2A ligand - produced activation of presynaptic 5-HT1A receptors and showed properties of a 5-HT2A receptor antagonist. Copyright
Bojarski, Andrzej J,Mokrosz, Maria J,Minol, Sijka Charakchieva,Koziol, Aneta,Wesolowska, Anna,Tatarczynska, Ewa,Klodzinska, Aleksandra,Chojnacka-Wojcik, Ewa
p. 87 - 95
(2007/10/03)

2-aminobenzoxazole derivatives and combinatorial libraries thereof
The present invention relates to novel 2-aminobenzoxazole derivative compounds of the following formula: wherein R1 to R4 and Z have the meanings provided herein. The invention further relates to combinatorial libraries containing two or more such compounds, as well as methods of preparing 2-aminobenzoxazole derivative compounds.
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(2008/06/13)

Pictet-Spengler condensation of N-sulfonyl-β-phenethylamines with α- chloro-α-phenylselenoesters. New synthesis of 1,2,3,4- tetrahydroisoquinoline-1-carboxylates
The reaction of N-sulfonyl-β-phenethylamines with α-chloro-a- phenylseleno acetate/propionate esters under Lewis acid promotion gives moderate to good yields of the corresponding 1,2,3, 4- tetrahydroisoquinoline-1-carboxylates. Varying degrees of diastereoselection were obtained using chiral sulfonamides and/or esters. Employing this strategy, the achievement of a new total synthesis of Calycotomine is reported.
Silveira, Claudio C.,Bernardi, Carmem R.,Braga, Antonio L.,Kaufman, Teodoro S.
p. 4969 - 4972
(2007/10/03)

Potential GABAB receptor antagonists. IX: The synthesis of 3-amino-3-(4-chlorophenyl)propanoic acid, 2-amino-2-(4-chlorophenyl)ethylphosphonic acid and 2-amino-2-(4-chlorophenyl)ethanesulfonic acid
This paper describes the synthesis of 3-amino-3-(4-chlorophenyl)propanoic acid and the corresponding phosphonic and sulfonic acids, lower homologues of baclofen, phaclofen and saclofen respectively. The chlorinated acids were all weak specific antagonists of GABA at the GABAB receptor, with the sulfonic acid (pA2 4·0) being stronger than the phosphonic acid (pA2 3·8) and carboxylic acid (pA2 3·5).
Abbenante, Giovanni,Hughes, Robert,Prager, Rolf H.
p. 523 - 527
(2007/10/03)

Process for the preparation of (8As,12AS,13AS)-decahydroisoquino ((2,1-G) (1,6)-naphthyridin-8-one derivatives
The invention provides a process for preparing single enantiomers of compounds represented by the formula: STR1 and chiral acid addition salts thereof; wherein: X and Y are independently hydrogen; lower alkyl; lower alkoxy; or halo; or X and Y taken together is methylenedioxy or ethylene-1,2-dioxy; which includes reduction of a compound represented by the formula: STR2 to give a mixture of stereoisomers represented by the formula: STR3 wherein each wavy line independently represents a bond in either the α or β position; followed by dissolving the mixture of stereoisomers and a chiral resolving acid in a suitable solvent and allowing the solution to crystallize, giving a salt of the desired enantiomer.
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(2008/06/13)

Enzymatic Preparation of Aromatic Ethylamines from Aromatic L-Amino Acids
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Nakazawa, Hidetsugu,Sano, Konosuke,Matsuda, Keizo,Mitsugi, Koji
p. 1210 - 1211
(2007/10/02)

SYNTHESIS OF SOME DERIVATIVES OF 1-PHENYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINE AND 11-PHENYL-5,6-DIHYDRO-11H-s-TRIAZOLO-3-BENZAZEPINE
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Vejdelek, Zdenek,Protiva, Miroslav
p. 2345 - 2350
(2007/10/02)

Amidines. VII. Hydrolysis and alcoholysis of carboxamides under mild conditions
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Ono,Araya,Todoriki,Tamura
p. 1824 - 1831
(2007/10/02)

Method of treating nausea and vomiting with certain substituted-phenylalkylamino (and aminoacid) derivatives and other serotonin depleting agents
A method for the treatment of emesis in a mammal, which method comprises administering to said mammal an emesis inhibiting amount of a compound which depletes serotonin in the brain of mammals; among which are compounds having the formula: STR1 wherein, R is selected from hydrogen, loweralkyl, trifluoromethyl, carboxyl, or loweralkoxycarbonyl; R1 and R2 are hydrogen or loweralkyl; Z is trifluoromethyl or halogen; the optical isomers and pharmaceutically acceptable salts thereof; two of the preferred compounds of the invention are fenfluramine and norfenfluramine.
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(2008/06/13)

Studies of Reduction with Dimethoxyborane-Transition Metal Salt Systems. I. Reduction of Nitriles, Aldehydes and Ketones with Dimethoxyborane-Transition Metal Salt Systems
The reduction of a variety of functional groups with new dimethoxyborane-transition metal salt systems was investigated.The dimethoxyborane-cobaltous chloride system reduced nitriles and aldehydes under mild conditions in good yields, and the dimethoxyborane-nickelous chloride system similarly reduced nitriles, aldehydes, olefin and ketones.The other functional groups tested were unaffected by these systems.Keywords reduction; nitrile; aldehyde; ketone; dimethoxyborane; transition metal salt; dimethoxyborane-cobaltous chloride system; dimethoxyborane-nickelous chloride system
Nose, Atsuko,Kudo, Tadahiro
p. 808 - 810
(2007/10/02)

Synthesis of Fused Heterocycles: 1,2,3,4-Tetrahydroisoquinolines and Ring Homologues via Sulphonamidomethylation
The title heterocycles (3) have been obtained by a two-step synthesis; namely an initial intramolecular sulphonamidomethylation of N-aralkylsulphonamides (1) in acid media followed by desulphonylation of compounds (2) under moderate conditions, either by reduction or acid hydrolysis.Generally both steps gave good or high yields of compounds (3) variously substituted in the aromatic ring and with a six-, seven-, or eight-membered heterocyclic ring.
Orazi, Orfeo O.,Corral, Renee A.,Giaccio, Hector
p. 1977 - 1982
(2007/10/02)

Diazaestrones and analogs. I. Pharmacological study and synthesis of heterosteroid analogs to establish structure-analgesic activity relationships
With the intention of showing the effect, about pharmacological properties, in replacing two estron asymetric carbon by nitrogen atoms and removal of angular methyl from steroid, stereospecific synthesis of 8,13-diazaestron and several substituted similar compounds was realized from β-1-(succinimidoethyl)-dihydroisoquinolines, precursors of a C open ring synthesis. The splitting of the 2-methoxydiazaestron methyl ester was carried out by mean of binaphthylphosphoric acid, and synthesis of several modified analogs of heterosteroid, was carried out to determine the effect of aromatic ring reduction, lactamic carbonyl reduction, and distance between 8 and 13 nitrogen atoms, about pharmacological activity. Hormonal, spasmolytic and analgesic activities were studied, good results were observed in analgesic activity.
Hocquaux,Marcot,Redeuilh,et al.
p. 319 - 329
(2007/10/02)

An Efficient Reduction Of Nitriles And Amides To The Corresponding Amines With Tetra-N-Butylammonium Borohydride In Dichloromethane
The reduction of nitriles and amides to the corresponding amines with tetra-n-butylammonium borohydride in dichloromethane has been reported, in which the other functional groups such as ester, nitro, and halogen attached to the aromatic ring are not affected.
Wakamatsu, Takeshi,Inaki, Harumi,Ogawa, Akemi,Watanabe, Masako,Ban, Yoshio
p. 1437 - 1440
(2007/10/02)

Cyclic carbamates as reagents for alkylamination of aromatic derivatives under friedel-crafts conditions
Aryl(ethyl-) and propylamines are obtained with good yields by a decarboxylation-alkylation process applied on aluminium trichloride-cyclic carbamate complexes. The coupling of two aromatic units is observed in the case of oxazolidinonetoluene reaction.
Jouitteau,Perchec,Forestiere,Silicon
p. 1719 - 1722
(2007/10/02)