6947-99-5Relevant academic research and scientific papers
2,3-Ethylene- and 2,3-trimethylene-bridged analogues of the group III metabotropic glutamate receptor ligand 2-amino-4-phosphonobutanoic acid
Johnson, Rodney L.,Rao, Kolluri S.S.P.
, p. 57 - 60 (2005)
The racemic trans- and cis-isomers of 1-amino-2-phosphonomethyl- cyclobutanecarboxylic acid (5 and 6) and 1-amino-2-phosphonomethyl- cyclopentanecarboxylic acid (7 and 8) were synthesized as extensions of the mGluR4 agonists trans- and cis-1-amino-2-phosphonomethyl-cyclopropanecarboxylic acid (3 and 4). Although the methylene bridge in 3 and 4 allows for retention of affinity toward the mGluR4 receptor, increasing the bridging unit to the ethylene group as in 5 and 6 or to the trimethylene group as in 7 and 8 introduces sufficient steric hindrance to eliminate affinity for the mGluR4 receptor.
Methods of synthesis of alicyclic 1,5,9-triketones. Reaction of transaminomethylation
Akimova,Soldatkina,Ivanenko, Zh. A.,Savchenko
, p. 720 - 728 (2017/07/07)
Alicyclic 1,5,9-triketones with various combination of 5-, 6-, 7-membereded cycles in the molecule were obtained by methods of diketone condensation, Michael reaction, and proceeding from Mannich mono- and bisbases and cycloalkanones. The latter method wa
PROCESS FOR PREPARATION OF NORBORNENE DERIVATIVES
-
Page/Page column 25, (2012/05/04)
A method for producing a norbornene derivative, comprising: a first step of forming a Mannich base by reacting a carbonyl compound and an amine compound with each other in an acidic solvent, to thereby obtain a reaction liquid comprising the Mannich base in the acidic solvent, the acidic solvent comprising a formaldehyde derivative and 0.01 mol/L or more of an acid represented by the formula: HX (In the formula, X represents F or the like), the carbonyl compound being represented by any of the following general formulae (1) to (3): [in formulae (1) to (3), R1, R2, R3, R4, R5, and R6 each independently represent a hydrogen atom or the like, and n represents an integer of any of 0 to 4], the amine compound being represented by the following general formula (4): [in the formula (4), R7S each independently represent a linear chain saturated hydrocarbon group having 1 to 20 carbon atoms or the like, and X- represents F- or the like], the Mannich base being represented by any of the following general formulae (5) to (7): [R1, R2, R3, R4, R5, R6, and n in the formulae (5) to (7) have the same meanings as those of R1, R2, R3, R4, R5, R6, and n in the formulae (1) to (3), and R7 and X- in the formulae (5) to (7) have the same meanings as those of R7 and X- in the formula (4)] and a second step of reacting the Mannich base and a diene compound with each other by adding an organic solvent, a base in an amount of 1.0 to 20.0 equivalents to the acid, and the diene compound to the reaction liquid, and then heating the reaction liquid, to thereby form a norbornene derivative, the diene compound being represented by the following general formula (8): [in the formula (8), R8 represents a hydrogen atom or the like], the norbornene derivative being represented by any of the following general formulae (9) to (11): [R1, R2, R3, R4, R5, R6, and n in the formulae (9) to (11) have the same meanings as those of R1, R2, R3, R4, R5, R6, and n in the formulae (1) to (3), and R8 in the formulae (9) to (11) has the same meaning as that of R8 in the formula (8)].
Further exploration of 1-{2-[Bis-(4-fluorophenyl)methoxy]ethyl}piperazine (GBR 12909): Role of N-aromatic, N-heteroaromatic, and 3-oxygenated N-phenylpropyl substituents on affinity for the dopamine and serotonin transporter
Lewis, David,Zhang, Ying,Prisinzano, Thomas,Dersch, Christina M.,Rothman, Richard B.,Jacobson, Arthur E.,Rice, Kenner C.
, p. 1385 - 1389 (2007/10/03)
A series of N-aromatic, N-heteroaromatic, and oxygenated N-phenylpropyl derivatives of 1-(2-benzhydryloxyethyl)-piperazine and 1-{2-[bis-(4-fluorophenyl)methoxy]ethyl}piperazine, analogues of GBR 12909 (1a) and 12935 (1b), was synthesized and examined for their dopamine (DAT) and serotonin (SERT) transporter binding properties. One of these compounds, racemic 3-[4-(2-benzhydryloxyethyl)piperazin-1-yl]-1-(3-fluorophenyl)-propan-1-ol (33), had DAT affinity as good as, or better than, GBR 12909 and 12935, and was more selective for DAT over SERT than the GBR compounds. Both trans- (43) and cis- (47) (±)-2-(4-{2-[bis-(4-fluorophenyl)-methoxy]ethyl}piperazin-1- ylmethyl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol had relatively good SERT selectivity and, as well, showed high affinity for SERT.
Reaction of Photochemically Generated Dibromocarbene with 1,2-Dimethylenecycloalkanes. 1,4 Addition Is Real
Le, Nguyet Anh,Jones, Maitland,Bickelhaupt, Friedrich,Wolf, Willem H. de
, p. 8491 - 8493 (2007/10/02)
Photochemically or thermally generated dibromocarbene adds to a variety of 1,2-dimethylenecycloalkanes and to norborndiene to give 1,2 and 1,4 addition products.The ratios of the products of the two addition types match those found from dibromocarbene generated from bromoform.Dibromocarbene is capable of 1,4 addition.
α-Aminoalkylation of Enamines with Iminiumtetrachloro-aluminates
Risch, Nikolaus,Esser, Achim
, p. 208 - 210 (2007/10/02)
We report the use of iminiumtetrachloro-aluminates 1a, 2a, and 3a in Mannich reactions.These salts are easily synthesized and offer some important advantages compared to iminium salts 1b-e. - Keywords: Iminiumtetrachloro-aluminates, Preformed Mannich Salts, α-Aminoalkylation, Enamines
A Convenient Regioselective Synthesis of Mannich Bases
Rochin, C.,Babot, O.,Dunogues, J.,Duboudin, F.
, p. 667 - 668 (2007/10/02)
A new, convenient regioselective process for aminomethylation of ketones is reported, involving the in situ formation of silyl enol ethers and iminium salts.
THE SYNTHESIS OF MANNICH BASES FROM KETONES AND ESTERS VIA ENAMINONES.
Schuda, Francis Paul,Ebner, Cynthia B.,Morgan, Tina M.
, p. 2567 - 2570 (2007/10/02)
The reactions of a series of activated methylene compounds with amide acetals to form high yields of enaminones is described.Further conversion to the Mannich bases via reduction with lithium aluminium hydride is also covered.
Nitrones and Oxaziridines. XXXI. Synthesis of Some Bicyclic 1-Pyrroline 1-Oxides
Black, David St. C.,Johnstone, Lynn M.
, p. 117 - 128 (2007/10/02)
The bicyclic 1-pyrroline 1-oxides (10), (11) and (13) have been prepared by reductive cyclization of the respective γ-nitro ketones (3), (4) and (6).Reduction of nitro ketone (2a) gave the unstable nitrone (7), which underwent dimerization to compound (8)
A NOVEL AMINOMETHYLATION OF SILYL ENOL ETHERS WITH AMINOMETHYL ETHERS CATALYZED BY IODOTRIMETHYLSILANE OR TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE
Hosomi, Akira,Iijima, Susumu,Sakurai, Hideki
, p. 547 - 550 (2007/10/02)
The iodotrimethylsilane-catalyzed reaction of silyl enol ethers with aminomethyl ethers in acetonitrile gives aminomethylation products of the corresponding ketones readily.The reaction can also be catalyzed by trimethylsilyl trifluoromethanesulfonate in dichloromethane.
