- Copper-catalyzed radical ring-opening halogenation with HX
-
An efficient copper-catalyzed radical ring-opening halogenation with HX (aq) is described. This protocol features redox-neutral conditions, green halogen sources, and a broad substrate scope, providing practical access to distally chlorinated, brominated and iodinated alkyl ketones and alkyl nitriles with moderate to good yields. This journal is
- Bai, Ming,Duan, Xin-Hua,Guo, Li-Na,Liu, Shuai,Sun, Qing-Xin,Xu, Peng-Fei
-
supporting information
p. 8652 - 8655
(2021/09/04)
-
- Intramolecular Cyclization of Brominated Oxime Ether Promoted with Ytterbium(0) to the Synthesis of Cyclic Imines
-
The first utility of ytterbium(0) as a mediating-metal in the intramolecular cyclization of brominated oxime ether was reported in this paper. In contrast to the prior methods, the N–O bond was used as a receptor of nucleophilic reagent, rather than as a source of N-centered radicals. Cyclic imines were obtained in this one-pot reaction with a broad scope of substrates and feasible reaction conditions.
- Wang, Yiqiong,Huang, Fei,Zhang, Songlin
-
supporting information
p. 5178 - 5181
(2020/08/13)
-
- Manganese-Catalyzed Electrochemical Deconstructive Chlorination of Cycloalkanols via Alkoxy Radicals
-
A manganese-catalyzed electrochemical deconstructive chlorination of cycloalkanols has been developed. This electrochemical method provides access to alkoxy radicals from alcohols and exhibits a broad substrate scope, with various cyclopropanols and cyclobutanols converted into synthetically useful β- and γ-chlorinated ketones (40 examples). Furthermore, the combination of recirculating flow electrochemistry and continuous inline purification was employed to access products on a gram scale.
- Allen, Benjamin D. W.,Hareram, Mishra Deepak,Seastram, Alex C.,McBride, Tom,Wirth, Thomas,Browne, Duncan L.,Morrill, Louis C.
-
p. 9241 - 9246
(2019/11/19)
-
- Iminyl Radicals by Reductive Cleavage of N-O Bond in Oxime Ether Promoted by SmI2: A Straightforward Synthesis of Five-Membered Cyclic Imines
-
A new generation method of N-centered radicals from the reductive cleavage of the N-O bond in oxime ether promoted by SmI2 is reported for the first time. The in-situ-generated N-centered radicals underwent intramolecular cyclization to afford five-membered cyclic imines in two manners: N-centered radical addition and N-centered anion nucleophilic substitution. From a synthetic point of view, an efficient synthetic method of five-membered cyclic imines was developed. A mechanism of the transformation was proposed.
- Huang, Fei,Zhang, Songlin
-
supporting information
p. 7430 - 7434
(2019/10/11)
-
- Visible-light-enhanced ring opening of cycloalkanols enabled by br?nsted base-tethered acyloxy radical induced hydrogen atom transfer-electron transfer
-
A metal-free ring opening/halogenation of cycloalkanols, which combines both PPO/TBAX oxidant system and blue LEDs irradiation, is presented. This method produces diverse γ, α, and even more remotely halogenated ketones in moderate to excellent yields under mild conditions. Interestingly, experimental and computational studies demonstrate the novel ring size-dependent concerted/stepwise (four-/five- to eight-membered rings) hydrogen atom transfer-electron transfer induced by Br?nsted base-tethered acyloxy radical, which indicates distinct advantages brought by the cyclic structure of diacyl peroxides.
- Zhao, Rong,Yao, Yuan,Zhu, Dan,Chang, Denghu,Liu, Yang,Shi, Lei
-
supporting information
p. 1228 - 1231
(2018/02/23)
-
- Biaryl Ketones by Suzuki–Miyaura Cross-Coupling of Organotrifluoroborates and Acyl Chlorides
-
A procedure for the synthesis of biaryl ketones by a palladium-catalyzed Suzuki–Miyaura cross-coupling reaction between phenyltrifluoroborates and benzoyl chlorides is described. Organotrifluoroborates are unique to other cross-coupling reagents as they have a high functional-group tolerance and are moisture-stable. Moderate to excellent yields were obtained for all substrates tested.
- Forbes, Alaina M.,Meier, G. Patrick,Jones-Mensah, Ebenezer,Magolan, Jakob
-
p. 2983 - 2987
(2016/07/11)
-
- Regioselective Synthesis of Carbonyl-Containing Alkyl Chlorides via Silver-Catalyzed Ring-Opening Chlorination of Cycloalkanols
-
A novel and regioselective approach to carbonyl-containing alkyl chlorides via silver-catalyzed ring-opening chlorination of cycloalkanols is reported. Concurrent C(sp3)-C(sp3) bond cleavage and C(sp3)-Cl bond formation efficiently occur with good yields under mild conditions, and the chlorinated products are readily transformed into other useful synthetic intermediates and drugs. The reaction features complete regioselectivity, high efficiency, and excellent practicality. (Chemical Equation Presented).
- Huang, Feng-Qing,Xie, Jian,Sun, Jian-Guo,Wang, Yue-Wei,Dong, Xin,Qi, Lian-Wen,Zhang, Bo
-
p. 684 - 687
(2016/03/01)
-
- Synthetic method of gamma-chlorobutanone derivatives
-
The invention discloses a synthetic method of gamma-chlorobutanone derivatives, and relates to a production method of inner-end and distal-end chlorinated aliphatic ketones in the technical field of chemical synthesis. Acetonitrile is taken as a solvent, manganese chloride is taken as a catalyst, tert-cyclobutanol, TMSCI (trimethylchlorosilane) and IBX (2-iodoxybenzoic acid) are subjected to a reaction, and a crude product is obtained; an organic solvent is removed through reduced-pressure concentration; the crude product is subjected to chromatography on a silica gel column with an organic solvent, and a refined product can be obtained. A synthetic route is shown in the specification, wherein R is aryl or alkyl. The raw materials used in the whole reaction process are cheap and easily available, a substrate adopted in the method has wide application range, and the whole reaction is simple and easy to operate and higher in yield; the reaction cost is reduced greatly.
- -
-
Paragraph 0027-0029
(2017/07/22)
-
- A combined computational and experimental investigation of the oxidative ring-opening of cyclic ethers by oxoammonium cations
-
The propensity of oxoammonium cations to facilitate the oxidative ring-opening of cyclic ethers to their corresponding distal hydroxy ketones is investigated. The reaction has been evaluated using experimental and computational methods to gain deeper insight into trends in reactivity.
- Loman, Jacob. J.,Carnaghan, Emma R.,Hamlin, Trevor A.,Ovian, John M.,Kelly, Christopher B.,Mercadante, Michael A.,Leadbeater, Nicholas E.
-
p. 3883 - 3888
(2016/05/24)
-
- The synthesis of ω-(2-aryl-1,3-dioxolan-2-yl)alkyl purine derivatives and their activity towards HIV reverse transcriptase
-
Novel derivatives of 6-substituted purines were synthesized by alkylation of 6-substituted purines with various 2-(chloroalkyl)-2-aryl-1,3-dioxolanes and related compounds. Their inhibitory properties toward HIV reverse transcriptase were studied. The structure-activity relationship within the synthesized compounds was found.
- Komissarov,Valuev-Elliston,Ivanova,Kochetkov,Kritzyn
-
-
- Selective oxidation of alcohols with alkali metal bromides as bromide catalysts: Experimental study of the reaction mechanism
-
A bromide-catalyzed oxidation of alcohols was developed which proceeded in the presence of an alkali metal bromide and an oxidant under mild conditions. The reaction involved an organic-molecule-free oxidation using KBr and Oxone and a Br?nsted acid assisted oxidation using KBr and aqueous H 2O2 solution to provide a broad range of carbonyl compounds in high yields. Moreover, the bromide-catalyzed oxidation of primary alcohols enabled the divergent synthesis of carboxylic acids and aldehydes under both reaction conditions in the presence of TEMPO. A possible catalytic mechanism was suggested on the basis of various mechanistic studies.
- Moriyama, Katsuhiko,Takemura, Misato,Togo, Hideo
-
p. 6094 - 6104
(2014/07/21)
-
- PROTEIN CROSSLINKING INHIBITOR AND USE OF THE SAME
-
The present invention relates to: a ketone compound having transglutaminase-inhibiting activity, which is represented by the following Formula 1, 2, or 3: wherein R1 is a substituted or unsubstituted aryl or heterocyclyl group, R2, R3, and R4 are hydrogen atoms, n is 2, X is halogen, R5 and R6 independently represent a hydrogen atom or a substituted or unsubstituted C1-C10 alkyl, aryl, or aralkyl group, wherein R5 and R6 are not hydrogen atoms at the same time, or R5 and R6 may be taken together to form a saturated or unsaturated and substituted or unsubstituted heterocyclyl group containing a nitrogen atom (N); an inhibitor of protein crosslinking comprising the compound; and a composition for preventing or treating a protein-crosslinking causative disease, which comprises the compound or the protein crosslinking inhibitor.
- -
-
Page/Page column 30
(2012/11/08)
-
- Silver-catalyzed decarboxylative chlorination of aliphatic carboxylic acids
-
Decarboxylative halogenation of carboxylic acids, the Hunsdiecker reaction, is one of the fundamental functional group transformations in organic chemistry. As the initial method requires the preparations of strictly anhydrous silver carboxylates, several modifications have been developed to simplify the procedures. However, these methods suffer from the use of highly toxic reagents, harsh reaction conditions, or limited scope of application. In addition, none is catalytic for aliphatic carboxylic acids. In this Article, we report the first catalytic Hunsdiecker reaction of aliphatic carboxylic acids. Thus, with the catalysis of Ag(Phen)2OTf, the reactions of carboxylic acids with t-butyl hypochlorite afforded the corresponding chlorodecarboxylation products in high yields under mild conditions. This method is not only efficient and general, but also chemoselective. Moreover, it exhibits remarkable functional group compatibility, making it of more practical value in organic synthesis. The mechanism of single electron transfer followed by chlorine atom transfer is proposed for the catalytic chlorodecarboxylation.
- Wang, Zhentao,Zhu, Lin,Yin, Feng,Su, Zhongquan,Li, Zhaodong,Li, Chaozhong
-
experimental part
p. 4258 - 4263
(2012/04/10)
-
- Azido carbonyl compounds as DNA cleaving agents
-
Irradiation of azido carbonyl compounds using UV light (≥310 nm) produced triplet alkyl nitrenes and aroyl radicals, which resulted in efficient cleavage of single strand DNA at pH 7.0. DNA cleaving ability of azido carbonyl compounds was found to be dependent on its concentration and substituents on its aromatic ring. Further, newly synthesized naphthalene based azido carbonyl compounds showed DNA cleavage ability at longer wavelength of UV light (≥350 nm) and also binding studies revealed that they bind to ct-DNA by weak intercalation mode.
- Chowdhury, Nilanjana,Dutta, Sansa,Karthick,Anoop, Anakuthil,Dasgupta, Swagata,Pradeep Singh
-
-
- Pyrazole-based sulfonamide and sulfamides as potent inhibitors of mammalian 15-lipoxygenase
-
A series of inhibitors of mammalian 15-lipoxygenase (15-LO) based on a 3,4,5-tri-substituted pyrazole scaffold is described. Replacement of a sulfonamide functionality in the lead series with a sulfamide group resulted in improved physicochemical properties generating analogs with enhanced inhibition in cell-based and whole blood assays.
- Ngu, Khehyong,Weinstein, David S.,Liu, Wen,Langevine, Charles,Combs, Donald W.,Zhuang, Shaobin,Chen, Xing,Madsen, Cort S.,Harper, Timothy W.,Ahmad, Saleem,Robl, Jeffrey A.
-
scheme or table
p. 4141 - 4145
(2011/08/06)
-
- Synthesis of 1-phenylbut-3-ene-1,2-dione and its attempted radical polymerization
-
1,2-Diketone moiety-bearing monomer 1-phenylbut-3-ene-1,2-dione, an analogue of phenyl vinyl ketone, was synthesized from 4-chlorobutyryl chloride in a 29 % overall yield in five steps. Following acylation of benzene with 4-chlorobutyryl chloride, the resulting α-methylene group was oxidized to 1,2-diketone in three steps: successive bromination, substitution with lithium hydroxide, and oxidation of α-hydroxyketone with potassium dichromate. The final step was dehydrochlorination of 4-chloro-1-phenyl-butane-1,2-dione. The attempted copolymerization of this monomer with styrene, using AIBN as the initiator, was unsuccessful.
- Husar, Branislav,Lukac, Ivan,Chmela, Stefan,Canet, Jean-Louis,Troin, Yves
-
experimental part
p. 499 - 503
(2011/11/06)
-
- Synthesis of 1-phenylbut-3-ene-1,2-dione and its attempted radical polymerization
-
1,2-Diketone moiety-bearing monomer 1-phenylbut-3-ene-1,2-dione, an analogue of phenyl vinyl ketone, was synthesized from 4-chlorobutyryl chloride in a 29 % overall yield in five steps. Following acylation of benzene with 4-chlorobutyryl chloride, the resulting ?±-methylene group was oxidized to 1,2-diketone in three steps: successive bromination, substitution with lithium hydroxide, and oxidation of ?±-hydroxyketone with potassium dichromate. The final step was dehydrochlorination of 4-chloro-1-phenyl-butane-1,2-dione. The attempted copolymerization of this monomer with styrene, using AIBN as the initiator, was unsuccessful.
- Hus??r, Branislav,Luk????, Ivan,Chmela, ??tefan,Canet, Jean-Louis,Troin, Yves
-
p. 499 - 503
(2015/03/03)
-
- Atom-efficient cross-coupling reactions of triarylbismuths with acyl chlorides under Pd(0) catalysis
-
The atom-efficient cross-coupling reaction of triarylbismuths with a variety of aliphatic, aromatic, and hetero-aromatic acyl chlorides was demonstrated to afford high yields of cross-coupled ketones under palladium catalysis. The corresponding cross-coupling reaction with diacid chlorides also furnished bis-coupled ketones in good yields.
- Rao, Maddali L.N.,Venkatesh, Varadhachari,Banerjee, Debasis
-
p. 12917 - 12926
(2008/03/28)
-
- Cationic palladium(II)-catalyzed addition of arylboronic acids to nitriles. One-step synthesis of benzofurans from phenoxyacetonitriles
-
(Chemical Equation Presented) A cationic palladium complex catalyzed addition of arylboronic acids to nitrites to yield aryl ketones with moderate to good yields was developed. A one-step synthesis of benzofurans from phenoxyacetonitriles under the catalysis of [(bpy)Pd+(μ-OH)] 2(-OTf)2 or [(bpy)Pd2+(H 2O2)2](-OTf)2 was developed which showed that the cationic palladium catalyst is highly active for these addition reactions.
- Zhao, Baowei,Lu, Xiyan
-
p. 5987 - 5990
(2007/10/03)
-
- Palladium(II)-catalyzed addition of arylboronic acid to nitriles
-
The addition of arylboronic acid to nitriles catalyzed by palladium(II) species in the presence of bipyridine as the ligand was developed. The use of bipyridine is crucial for changing the properties of arylpalladium species from more electrophilic to more nucleophilic making the reaction possible.
- Zhao, Baowei,Lu, Xiyan
-
p. 6765 - 6768
(2007/10/03)
-
- Polymethylene derivatives of nucleic bases with ω-functional groups: V. Pyrimidine- and purine-containing γ-butyrophenones
-
New polymethylene derivatives of nucleic bases containing a keto function in the ω-position were synthesized by alkylation of nucleic bases with 2-(3-chloropropyl)-2-phenyl-1,3-dioxolane and the subsequent deblocking of the keto group; their physicochemical properties were studied.
- Kritzyn,Komissarov
-
p. 549 - 555
(2007/10/03)
-
- Copper-Mediated, Palladium-Catalyzed Coupling of Thiol Esters with Aliphatic Organoboron Reagents
-
Thiol esters and B-alkyl-9-BBN derivatives couple in the presence of a copper(I) carboxylate mediator and a palladium catalyst. In contrast to copper-mediated, palladium-catalyzed cross-couplings of thioorganics with boronic acids, the current coupling reaction of 9-BBN derivatives is facilitated by the addition of a base such as Cs2CO3. Under optimized conditions, a variety of thiol esters react with different B-alkyl-9-BBN derivatives giving ketones in moderate to excellent yields.
- Yu, Ying,Liebeskind, Lanny S.
-
p. 3554 - 3557
(2007/10/03)
-
- Selective oxidation of benzylic substrates to their corresponding carbonyl compounds with 3,6-Bis(triphenylphosphonium)cyclohexene peroxodisulfate
-
3,6-Bis(triphenylphosphonium)cyclohexene peroxodisulfate (BTPCP) was found to be a highly effective and selective oxidant for the conversion of benzyl monohalides, nitrils, and amines to their corresponding carbonyl compounds under mild and neutral conditions.
- Badri, Rashid,Soleymani, Mousa
-
p. 1325 - 1332
(2007/10/03)
-
- Ethyl Mandelate as a Convenient New Benzoyl Anion Equivalent
-
Ethyl mandelate acts as a convenient benzoyl anion equivalent for the formation of alkyl aryl ketones by deprotonation-alkylation followed by flash vacuum pyrolysis.
- Aitken, R. Alan,Thomas, Andrew W.
-
p. 293 - 294
(2007/10/03)
-
- Synthesis of Alkyl and Aryl Cyclopropyl Ketones
-
A series of cyclopropyl ketones are prepared by reactions of organometallic compounds with cyclopropanecarboxylic acid derivatives and also by cyclization of γ-chloro ketones.
- Matveeva,Kvasha,Kurts
-
-
- Photochemistry of nonconjugated diketones: internal self-quenching and energy transfer
-
The triplet state behavior of nine α,ο-dibenzoylalkanes indicates the occurrence of a rapid quenching interaction between the two carbonyl groups.This quenching is fastest (k=3E7 s-1) in dibenzoylbutane, is slightly slower (ca.E7 s-1) in dibenzoylethane, dibenzoylpentane, and 2,2-dibenzoylpropane, but is absent in 1,3-dibenzoylpropane.It also occurs in several "mixed" 1,4-diaroylbutanes incorporating p-ethylbenzoyl or p-methoxybenzoyl chromophores.This internal self-quenching is interpreted as the intramolecular counterpart of the well-know bimolecular self-quenching of aryl ketones, although no exact mechanism can be proposed.Such internal quenching does not occur as rapidly, if at all, in three "turned around" diketones: δ-(p-acetylphenyl)valerophenone, δ-(p-acetylphenoxy)valerophenone, and γ-(p-acetylphenoxy)butyrophenone.This fact, together with the varying rates of internal self-quenching in the dibenzoylalkanes, indicates the necessity for a very specific and close orientation of the two carbonyl groups for self-quenching.In the mixed diketones containing a p-alkylbenzoyl group, triplet excitation appears to be fully equilibrated between the two chromophores.However, in those containing a p-methoxybenzoyl group, excitation does not fully equilibrate before triplet decay, as evidenced by different quenching efficiencies for products from the two carbonyls.Analysis indicates intramolecular energy transfer rate constants -1.These are sufficiently lower than in other bichromophoric systems to suggest relatively slow energy hopping in the polymers of phenyl vinyl ketone.Key words: nonconjugated diketones, dibenzoylalkanes, sefl-quenching, energy transfer, triplet ketones.
- Wagner, Peter J.,Frerking, Harlan W. Jr.
-
p. 2047 - 2061
(2007/10/03)
-
- Piperdine and piperazine derivatives, and antihistaminic pharmaceutical compositions containing the same
-
Disclosed is a compound represented by Formula (I): STR1 wherein Ar1, Ar2, n, A, B and Z are as defined in claims. Disclosed are also a process for preparing the compound and pharmaceutical compositions containing the compound. The compound has an antihistamic and antiallergic effect.
- -
-
-
- PHOTODECARBOXYLATIVE CHLORINATION OF CARBOXYLIC ACIDS VIA THEIR BENZOPHENONE OXIME ESTERS
-
Decarboxylative chlorination of various aromatic and aliphatic carboxylic acids is performed successfully by the photolysis of their benzophenone oxime esters in carbon tetrachloride and corresponding chloro compounds are prepared in good yields.High selective generation of the certain radical and efficiency of the stable radical precursor, benzophenone oxime ester, afford much advantage for radical chemistry.
- Hasebe, Masato,Tsuchiya, Takashi
-
p. 6287 - 6290
(2007/10/02)
-
- Intramolecular Charge-Transfer Interactions in Triplet Keto Sulfides
-
The photochemistry of β-,γ-and δ-phenacyl sulfides, sulfoxides, and sulfones has been studied.The first group undergoes no irreversible reaction.The other two undergo type II photoelimination but in low quantum efficiency.Analysis of triplet lifetimes and product quantum yields indicates that all undergo rapid internal quenching, which is ascribed to a charge-transfer (CT) process.The positional dependence of rate constants for this CT reaction is β > γ > α >> δ > ε .Some rate constants (units of 1E8 s-1) for PhCO(CH2)nSBu are as follows: n = 1, 16; n = 2, 55; n = 3, 29; n = 4 ,1.7; n = 5, PhS BuS(O) >> BuS, BuSO2, CH3CO-S and range from 1E9-3*1E5 s-1.Rate constants for triplet state γ-hydrogen abstraction were found to correlate well with the ?1 values of the various sulfur groups, except for δ-sulfinyl, which apparently participates in the reaction.
- Wagner, Peter J.,Lindstrom, Michael J.
-
p. 3057 - 3062
(2007/10/02)
-
- Synthesis of Nitriles from Haloesters, Haloketones and Haloethers
-
The action of NaCN on haloesters, haloketones and haloethers has been studied.Haloesters wherein halogen and ester functions are located on adjacent carbon atoms, do not furnish the corresponding nitriles, whereas those with halogen and ester functions not located on adjacent carbon atoms, furnish the corresponding nitriles in good yields.The presence of hydroxy or ether function on the carbon adjacent to primary halide bearing carbon atom does not interfere in the reaction with cyanide. δ-Haloketones are transformed to ketonitriles, γ-Haloketones are transformed to cyclopropyl ketones and epoxyhalides to epoxynitriles.
- Talekar, D. G.,Joshi, P. L.,Ramaiah, P.,Rao, A. S.
-
p. 145 - 151
(2007/10/02)
-
- Scope, Limitation, and Mechanism of the Homoconjugate Electrophilic Addition of Hydrogen Halides
-
Hydrogen halides (HCl, HBr, HI) add by a homoconjugate 1,5 mechanism to cyclopropanes carrying certain electron-withdrawing substituents.When the substituent is COCH3, COC6H5, CO2H, or CN, the reaction gives the 1,3-disubstituted propane in high yield.Addition of DCl gives a product with deuterium only in the position α to the substituent.The order of rates is not in agreement with a mechanism whereby the cyclopropane ring is protonated initially, since the rate of such a process should be slowed by electron-withdrawing groups.The ketones, however, react much more rapidly than benzylcyclopropane, a model for the direct protonation mechanism.The homoconjugate mechanism involves rapid protonation of the side chain, followed by nucleophilic attack on the cyclopropane ring.The reaction is limited to substrates that can be protonated on the side chain to produce an intermediate with charge ajacent to the cyclopropane ring.This charge must be able to be transmitted by resonance to the unsubstituted ring positions in order to facilitate the nucleophilic step.
- Lambert, Joseph B.,Napoli, James J.,Johnson, Katharine Kappauf,Taba, Kalulu N.,Packard, Beverly Sue
-
p. 1291 - 1295
(2007/10/02)
-
- Modern Friedel-Crafts chemistry XIII. Intra- and intermolecular cyclization of some carbonyl derivatives under Friedel-Crafts conditions
-
Carbonyl group deactivation in the cycloalkylation of aryl haloalkyl ketones was studied.Ketones 1-5 were prepared and subjected to treatment with AlCl3, AlCl3/H2SO4 and H2SO4 catalysts.Whereas AlCl3 catalyst gave no cyclization products, the use of AlCl3/H2SO4 and H2SO4 catalysts afforded the corresponding indanones and/or tetralones (6-11).The intermediate p-methylacrylophenone (12) was also obtained in the case of ketone 2.Furthermore intermolecular cyclizations of benzene, toluene and p-xylene with 3-chloropropionyl chloride (13) and 4-chlorobutyryl chloride (14) were investigated.In the presence of AlCl3/CH3NO2 catalyst, only the corresponding aryl haloalkyl ketones (1-5) were formed whereas the use of AlCl3 catalyst gave, in addition, some cyclic ketones.However, the use of AlCl3/H2SO4 catalyst gave only the corresponding cyclic ketones (6-11).Results are discussed and mechanisms are suggested.In conclusion, carbonyl group deactivation for ring closure is demonstrated in the investigated ketones and cyclization can only effected under strenuous conditions.
- Khalaf, Ali A.,Abdel-Wahab, Aboel-Magd A.,El-Khawaga, Ahmed M.,El-Zohry, Maher F.
-
p. 285 - 291
(2007/10/02)
-
- 4-Arylcyclohexylamines
-
The invention relates to novel 4-hydroxymethyl(acyloxymethyl and methyl)-4-arylcyclohexylamines embraced by the formula SPC1 Wherein Ar is an aromatic ring selected from the group consisting of phenyl and naphthyl, each of which has from zero through three substituents independently selected from the group consisting of fluorine, chlorine, bromine, lower alkyl of one through three carbon atoms, lower alkoxy of one through three carbon atoms, and lower alkylthio of one through three carbon atoms; Z is selected from the group consisting of hydrogen, hydroxy and lower acyloxy of one through four carbon atoms; ? is a generic expression denoting cis and trans stereoconfiguration and mixtures thereof, with the proviso that when the stereoconfiguration of the linkage connecting the cyclohexane ring and CH2 Z is cis to the amino group, the linkage connecting the cyclohexane and Ar rings is trans, and vice versa; R1 is selected from the group consisting of hydrogen and lower alkyl of one through three carbon atoms; R2 is selected from the group consisting of hydrogen, lower alkyl of one through three carbon atoms, EQU1 WHEREIN N IS 2 THROUGH 5 AND Ar has the same meaning as above; R1 and R2 taken together with --N is a saturated heterocyclic amino radical selected from the group consisting of unsubstituted and substituted pyrrolidino, piperidino, hexamethylenimino, morpholino and piperazino; and pharmacologically acceptable acid addition salts thereof. It also relates to intermediates and processes for the preparation of the aforesaid novel compounds (I) and novel derivatives thereof. The administration to humans and animals of the novel compounds (I) depresses their central nervous systems and lowers their blood pressures.
- -
-
-