- Cobalt-bridged secondary building units in a titanium metal-organic framework catalyze cascade reduction of N-heteroarenes
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We report here a novel Ti3-BPDC metal-organic framework (MOF) constructed from biphenyl-4,4′-dicarboxylate (BPDC) linkers and Ti3(OH)2 secondary building units (SBUs) with permanent porosity and large 1D channels. Ti-OH groups from neighboring SBUs point toward each other with an O-O distance of 2 ?, and upon deprotonation, act as the first bidentate SBU-based ligands to support CoII-hydride species for effective cascade reduction of N-heteroarenes (such as pyridines and quinolines) via sequential dearomative hydroboration and hydrogenation, affording piperidine and 1,2,3,4-tetrahydroquinoline derivatives with excellent activity (turnover number ～ 1980) and chemoselectivity.
- Feng, Xuanyu,Song, Yang,Chen, Justin S.,Li, Zhe,Chen, Emily Y.,Kaufmann, Michael,Wang, Cheng,Lin, Wenbin
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p. 2193 - 2198
(2019/02/20)
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- Photochemical Cleavage of Benzylic C-N Bond to Release Amines
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The 3-(diethylamino)benzyl (DEABn) group has been studied for releasing primary, secondary, and tertiary amines by direct photochemical breaking of the benzylic C-N bond. While photochemical release of primary and secondary amines provides high yields in
- Wang, Pengfei,Devalankar, Dattatray A.,Lu, Wenya
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p. 6195 - 6200
(2016/08/16)
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- 1,4-Diphenalkylpiperidines: A new scaffold for the design of potent inhibitors of the vesicular monoamine transporter-2
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A series of 1,4-diphenalkylpiperidine analogs were synthesized and evaluated for their affinity and inhibitory potency at the [3H]dihydrotetrabenazine (DTBZ) binding site and [3H]dopamine (DA) uptake site on the vesicular monoamine transporter-2 (VMAT2). Results revealed that translocation of the phenethyl side chains of lobelane from C2 and C6 to C1 and C4 around the central piperidine ring slightly reduces affinity and inhibitory potency at VMAT2 with respect to lobelane. However, methoxy and fluoro-substitution of either phenyl ring of these 1,4-diphenethyl analogs afforded VMAT2 inhibition comparable or higher (5-fold) affinity at the DTBZ binding and DA uptake sites relative to lobelane, whereas replacement of the 4-phenethyl moiety in these analogs with a 4-phenmethyl moiety markedly reduced affinity for the DTBZ binding and DA uptake sites by 3- and 5-fold, respectively. Among the twenty five 1,4-diphenethylpiperidine analogs evaluated, compounds containing a 4-(2-methoxyphenethyl) moiety exhibited the most potent inhibition of DTBZ binding and vesicular DA uptake. From this subgroup, analogs 8h, 8j and 8m exhibited Ki values of 9.3 nM, 13 nM and 13 nM, respectively, for inhibition of [3H]DA uptake by VMAT2, and represent some of the most potent inhibitors of VMAT2 function reported thus far.
- Nickell, Justin R.,Culver, John P.,Janganati, Venumadhav,Zheng, Guangrong,Dwoskin, Linda P.,Crooks, Peter A.
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p. 2997 - 3000
(2016/06/13)
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- METHOD FOR DEPROTECTING ARYL OR ALKYL SULFONAMIDES OF PRIMARY OR SECONDARY AMINES
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The invention relates to a method for removing an alkyl sulfonyl or aryl sulfonyl protecting group from a primary or secondary amine by contacting an alkyl sulfonamide or an aryl sulfonamide with a Stage 0 or Stage I alkali metal-silica gel material in the presence of a solid proton source under conditions sufficient to form the corresponding amine. The invention also relates to a method for removing an alkyl sulfonyl or aryl sulfonyl protecting group from a primary or secondary amine by a) reacting an alkyl sulfonamide or an aryl sulfonamide with a Stage 0 or Stage I alkali metal-silica gel material, and b) subsequently reacting the reaction product from step a) with an electrophile or a proton source. Preferred Stage 0 or Stage I alkali metal-silica gel materials include Na, K2Na, and Na2K.
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Page/Page column 7
(2009/12/24)
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- Alkali metals in silica gel (M-SG): A new reagent for desulfonation of amines
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(Chemical Equation Presented) A novel method for the desulfonation of secondary amines is described. Alkali metals absorbed into nanostructured silica (M-SG) were found to be useful solid-state reagents for the desuffonation of a range of N,N-disubstituted sulfonamides. M-SG reagents are room-temperature- stable free-flowing powders that retain the chemical reactivity of the parent metal, decreasing the danger and associated cost of using reactive metals.
- Nandi, Partha,Redko, Mikhail Y.,Petersen, Kathryn,Dye, James L.,Lefenfeld, Michael,Vogt, Paul F.,Jackson, James E.
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supporting information; experimental part
p. 5441 - 5444
(2009/06/18)
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- Deacylation of esters, thioesters and amides by a naphthalene-catalysed lithiation
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The reaction of different esters, thioesters and amides derived from pivalic, benzoic and 4-tert-butylbenzoic acids with an excess of lithium and a catalytic amount of naphthalene (8 mol%) led, after methanolysis, to the corresponding alcohols, thiols and amines, respectively, through a reductive non-hydrolytic procedure. This methodology represents a reasonable alternative to other non-reductive protocols. Georg Thieme Verlag Stuttgart.
- Behloul, Cherif,Guijarro, David,Yus, Miguel
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p. 309 - 314
(2007/10/03)
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- Reductive amination of aldehydes and ketones to their corresponding amines with NaBH4 in micellar media
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A variety of aliphatic and aromatic aldehydes and ketones were efficiently reduced to their corresponding amines when treated with primary and secondary amines and NaBH4 in micellar media at room temperature under neutral conditions. Springer-Verlag 2005.
- Alinezhad, Heshmatollah,Tajbakhsh, Mahmood,Salehian, Fatemeh
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p. 2029 - 2033
(2007/10/03)
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- Desilylation procedure via a naphthalene-catalysed lithiation reaction
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The reaction of silyl protected alcohols, amines and thiols with lithium powder and a catalytic amount of naphthalene, in THF, at 0°C led, after hydrolysis, to the recovery of the free alcohols, amines and thiols in very good yields. At least a phenyl group was required in the silyl protecting group for the success of the reaction. Some polyfunctionalised starting materials have successfully been deprotected. The stereochemical outcome of the deprotection of a silylated chiral secondary alcohol has also been studied and no racemization was observed. The process has shown to be a good alternative to the acid-catalysed desilylation procedures, the latter being not useful for the deprotection of some silylated tertiary alcohols.
- Behloul, Cherif,Guijarro, David,Yus, Miguel
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p. 6908 - 6915
(2007/10/03)
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- Detritylation of N-tritylamines via a naphthalene-catalyzed lithiation process
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The reaction of aliphatic and aromatic secondary and tertiary N-tritylamines 1 with lithium powder and a catalytic amount of naphthalene led to reductive detritylation, affording the corresponding amines 2 in good to excellent yields. The trityl group could selectively be removed in the presence of an allyl or a benzyl group. The detritylation process could successfully be extended to several hydroxy, alkoxy and amino functionalized N-tritylamines. The chemoselectivity between the trityl-nitrogen and the trityl-oxygen bond cleavages was also studied. This methodology represents an efficient deprotection of N-tritylamines under nonacidic reaction conditions.
- Behloul, Cherif,Guijarro, David,Yus, Miguel
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p. 1274 - 1280
(2007/10/03)
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- Cleavage of sulfonamides with phenyldimethylsilyllithium
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The toluene-p-sulfonamides of secondary amines and indoles are cleaved by treatment with phenyldimethylsilyllithium to give the secondary amines. Aziridine toluene-p-sulfonamides, however, are opened by attack of the silyllithium reagent on carbon to give β-silylethyl sulfonamides. The aziridine toluene-p-sulfonamide 22 derived from norbornene is different in giving the 2-[dimethyl(phenyl)silyl]-4-methylbenzenesulfonamide 23 of exo-norbornylamine. The aziridine toluene-p-sulfonamides 26, 28 and 30, derived from methyl cinnamate, methyl acrylate and cinnamyl acetate, are also anomalous, giving 3-[N-(p-tolylsulfonyl)amino]-3-phenylpropionic acid 27, {3-[N-(p-tolylsulfonyl)amino]propionyl}-dimethyl(phenyl)silane 29 and trans-cinnamyl alcohol 31, respectively, each derived by opening of the aziridine ring followed by loss of the silyl group.
- Fleming, Ian,Frackenpohl, Jens,Ila, Hiriyakkanavar
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p. 1229 - 1235
(2007/10/03)
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- POLYCYCLIC AMINE COMPOUNDS AND THEIR ENANTIOMERS, THEIR METHOD OF PREPARATION AND PHARMACEUTICAL COMPOSITIONS IN WHICH THEY ARE PRESENT
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The invention relates to polycyclic amine compounds of formula (I) STR1 where Y. m. Ar', n, p, Q, T, q and Z are defined herein. The invention also relates to methods of making the compounds of formula (I) and pharmaceutical compositions which contain the compounds of formula (I) . The inventive compounds are useful as neurokinin receptor antagonists, and are useful for the treatment of any substance P-dependent and neurokinin-dependent pathological condition.
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- 1-(benzylpiperidino)propan-2-ol derivatives, their preparation, their use as antimicrobial agents and the products in which they are present
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The invention relates to compounds of the formula: STR1 in which: Ar represents a phenyl group substituted by R2, R3 and R4, or a naphth-1-yl or naphth-2-yl group, unsubstituted or substituted by 1 or 2 halogen atoms; X represents an oxygen atom or a sulfur atom; R1 represents H or a halogen atom; R2 represents a halogen atom, a trifluoromethyl group, a phenyl group which is unsubstituted by 1 or 3 halogen atoms, a benzyl group which is unsubstituted or substituted by 1 to 3 halogen atoms, a phenoxy group which is unsubstituted or substituted by 1 to 3 halogen atoms, or a C1 -C4 alkyl group; R3 and R4 represents H, a halogen atom or a C1 -C4 alkyl group; and the benzyl group substitutes the piperidino radical in the 2-, 3- or 4-position, and their salts with mineral or organic acids. It also relates to a process for the preparation of said compounds and their use as antimicrobial agents, as antiseptic, disinfectant, preservative in different kinds of products (pharmaceutical compositions, cosmetics, agri-foodstuffs). It also relates to said products containing the compounds of formula (I).
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- Pharmaceutically-active phthalazine compounds
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Compounds having the formula STR1 wherein R is 2-[1-oxo-(2H)-phthalazinyl], R1, R2, R3, R4, R5, R6, X, Y, m and n have the meanings shown in the description. The compounds of formula I are pharmaceutically active as anti-vasospastic, anti-aggregating, and anti-proliferative agents.
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- Bronchodilating piperidinoethyl benzopyranopyridinones
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Disclosed are novel substituted benzopyranopyridines which are active as bronchodilators.
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