36648-32-5Relevant academic research and scientific papers
Versatile synthesis of novel tetrahydroquinolines as potentially active semicarbazide-sensitive amine oxidase (SSAO) inhibitors via tert-Amino effect
Deme, Ruth,Schlich, Michele,Mucsi, Zoltán,Karvaly, Gellért,Tóth, Gergo,Mátyus, Péter
, p. 164 - 196 (2016/10/22)
Several aminomethyl tetrahydroquinoline derivatives were synthesized in a facile three-ste procedure, in order to develop a semicarbazide-sensitive amine oxidase (SSAO) inhibitor library as proved by in vitro test on rat aorta microsomal fraction. The eff
Out-Basicity of 1,8-bis(dimethylamino)naphthalene: The experimental and theoretical challenge
Ozeryanskii, Valery A.,Pozharskii, Alexander F.,Antonov, Alexander S.,Filarowski, Alexander
, p. 2360 - 2369 (2014/04/03)
A possibility of non-conventional two-step protonation of 1,8-bis(dimethylamino)naphthalene (proton sponge) is discussed. Unlike the generally accepted mechanism, involving relatively slow direct penetration of a proton into the cleft between the peri-NMe2 groups, it consists of the rapid addition of a proton to the out-inverted NMe2 group with the subsequent slower rotational transfer of the proton into the inter-nitrogen space to produce a stable chelated cation. The following approaches were employed during the work: (1) competitive hydrogen bond formation in a specially designed alcohol in which the OH group might chelate either the proton sponge 1-NMe2 group or another basic center (N,N-dimethylaniline) of known basicity; (2) measuring the basicity of naphtho[1,8-b,c]diazabicyclo[3.3.3] undecane considered to be a close analogue of the proton sponge capable exclusively of out-protonation; (3) X-ray, spectral and DFT studies of structure, energy and stereodynamics of compounds obtained, including their conformers. For the first time, the pKa value of an organic base with a perfectly flat nitrogen atom is reported. The final conclusion is made that both pathways of proton sponge protonation, traditional and non-conventional, contribute in parallel with a still undefined ratio. The estimated out-basicity of the proton sponge is at least 5.5 orders of magnitude lower than the directly measured in-basicity. the Partner Organisations 2014.
Ortho-ketimines of 1,8-bis(dimethylamino)naphthalene: Synthesis, hydrolytic stability and transfer of basicity from proton sponge moiety to the imino function
Antonov, Alexander S.,Mikshiev, Vladimir Y.,Pozharskii, Alexander F.,Ozeryanskii, Valery A.
, p. 3273 - 3282 (2015/02/02)
A series of 2-ketimines and 2,7-diketimines of 1,8-bis(dimethylamino)naphthalene (proton sponge, DMAN) have been obtained and converted into the corresponding ketones via acidic hydrolysis. Investigation of structural and spectral properties of DMAN-based imines led to the conclusion that their unusual hydrolytic stability results from a combination of different factors the most important of which is a strong electron-donor effect of peri-dimethylamino groups.
Synthesis of o -(dimethylamino)aryl ketones, acridones, acridinium salts, and 1 H -indazoles by the reaction of hydrazones and arynes
Dubrovskiy, Anton V.,Larock, Richard C.
, p. 11232 - 11256 (2013/02/23)
A novel, efficient route to biologically and pharmaceutically important o-(dimethylamino)aryl ketones, acridones, acridinium salts, and 1H-indazoles has been developed starting from readily available hydrazones of aldehydes and o-(trimethylsilyl)aryl triflates. The reaction proceeds through arynes under mild conditions, tolerates a wide range of functional groups, and provides the final products in good to excellent yields.
Synthesis of o -(dimethylamino)aryl ketones and acridones by the reaction of 1,1-dialkylhydrazones and arynes
Dubrovskiy, Anton V.,Larock, Richard C.
supporting information; experimental part, p. 4136 - 4139 (2011/10/12)
A novel, efficient route to biologically and pharmaceutically important o-(dimethylamino)aryl ketones and acridones has been developed starting from readily available 1,1-dimethylhydrazones of aldehydes and o-(trimethylsilyl)aryl triflates. The reaction proceeds under mild conditions, tolerates a wide range of functional groups, and provides the final products in good to excellent yields.
Friedel-crafts acylation of arenes with carboxylic acids using polystyrene-supported aluminum triflate
Boroujeni, Kaveh Parvanak,Parvanak, Kamran
experimental part, p. 155 - 163 (2012/01/02)
Cross-linked polystyrene-supported aluminum triflate (Ps-Al(OTf) 3) has been shown to be a mild, efficient, and chemoselective heterogeneous Lewis acid catalyst for the acylation of aromatic compounds. The catalyst can be easily prepared from cheap starting materials, is stable (as a bench top catalyst) and is reusable.
Friedel-Crafts acylation of arenes with carboxylic acids using silica gel supported AlCl3
Parvanak Boroujeni, Kaveh
experimental part, p. 621 - 630 (2010/11/04)
Aromatic compounds react smoothly with carboxylic acids in the presence of silica gel supported aluminium trichloride to afford the corresponding ketones with high regioselectivity in high to excellent yields. The catalyst is stable (as a bench top catalyst) and can be easily recovered and reused without appreciable change in its efficiency. tuebitak.
Asymmetric synthesis of 1,3-diamines by diastereoselective reduction of enantiopure n-tert-butanesulfinylketimines: unusual directing effects of the ortho-substituent
Martjuga, Marina,Shabashov, Dmitry,Belyakov, Sergey,Liepinsh, Edvards,Suna, Edgars
supporting information; experimental part, p. 2357 - 2368 (2010/07/02)
(Figure Presented) Chiral, nonracemic 1,3-diamines were prepared in a highly diastereoselective reduction of diaryl N-tert-butanesulfinylketimines. Correlation between facial selectivity of the reduction and E or Z geometry of the starting ketimines suggests involvement of a cyclic transition state for the reduction. The ortho-substituent controls the geometry of N-tert- butanesulfinylketimines in the solid state and provides additional stabilization of the cyclic transition state.
Thermal decomposition of N-alkylated-2-amino-benzophenones
Creencia, Evelyn Cuevas,Takashashi, Atsushi,Horaguchi, Takaaki
experimental part, p. 1549 - 1556 (2009/12/24)
Thermal decomposition of N-alkylated 2-aminobenzophenones 1a-d was studied at 400-560 °C, using calcium oxide as catalyst. The reactions yielded both 5- and 6-membered heterocyclic compounds. The N-methylated-2-aminobenzophenones 1a-b decomposed at 400-56
Unusual aminations with tetramethylguanidine
Gabbutt, Christopher D.,Heron, B. Mark,McCreary, Janice M.,Thomas, David A.
, p. 69 - 71 (2007/10/03)
Heating activated halobenzenes with 1,1,3,3-tetramethylguanidine affords mixtures of dimethylaminobenzenes and 2-aryl-1,1,3,3-tetramethylguanidines.
