13652-31-8Relevant articles and documents
Determination of the conformations and relative configurations of exocyclic amines
Montalvo-gonzlez, J. Ascencin,Iniestra-galindo, Maria Guadalupe,Ariza-castolo, Armando
body text, p. 938 - 944 (2011/07/30)
The conformations and relative configurations of 20 amines, classified according to the following labeling scheme, were analyzed. Series a comprised compounds derived from N-(1-phenylethyl)cyclohexanamine, b comprised derivatives of N-[1-(naphthalen-2-yl)ethyl]cyclohexanamine, c comprised derivatives of N-(diphenylmethyl)cyclohexanamine, and d comprised derivatives of N-(propan-2-yl)cyclohexanamine. The compounds were labeled as follows: 1 indicates cyclohexanamine, 2 indicates 2-methylcyclohexanamines, 3 indicates 3-methylcyclohexanamines, 4 indicates 4-methylcyclohexanamines, and 5 indicates 4-tert-butylcyclohexanamines. These compounds were prepared without the use of stereoselective induction and, therefore, all expected stereoisomers were observed. Structural assignments were established by 1H, 13C, and 15N NMR.
First straightforward synthesis of 2,4-disubstituted benz[g]isoquinoline-3,5,10(2H)-triones, 1,2,3,5-substituted naphtho[3,2,1-de]isoquinoline-4,7-diones, and 6-substituted benzo[h]pyrido[3,4,5-kl]-1,2,3,4-tetrahydroacridine-5,8-diones
Jacobs, Jan,Kesteleyn, Bart,De Kimpe, Norbert
, p. 7545 - 7554 (2008/12/20)
Structural modifications to the benz[g]isoquinoline skeleton of N-substituted benz[g]isoquinoline-3,5,10(2H)-triones were envisaged in order to make future SAR studies possible for this type of bioactive compounds. Several N-substituted benz[g]isoquinoline-3,5,10(2H)-triones were converted to novel 2,4-substituted benz[g]isoquinoline-3,5,10(2H)-triones, new tetracyclic 1,2,3,5-substituted naphtho[3,2,1-de]isoquinoline-4,7-diones, and 6-substituted benzo[h]pyrido[3,4,5-kl]-1,2,3,4-tetrahydroacridine-5,8-diones. All the synthesized target compounds represent new heterocyclic systems, which were previously undescribed in the literature.
Silica gel supported sodium hydrogen sulfate as an efficient and reusable heterogeneous catalyst for the synthesis of imines in solvent-free conditions under microwave irradiation
Gopalakrishnan, Mannathusamy,Sureshkumar, Purushothaman,Kanagarajan, Vijayakumar,Thanusu, Jeyaraman,Govindaraju, Ramalingam
, p. 299 - 303 (2007/10/03)
This synthesis of imines has been carried out efficiently by the condensation of carbonyl compounds with amines in the presence of silica gel supported sodium hydrogen sulfate (NaHSO4.SiO2) as a heterogeneous catalyst under microwave irradiation in solvent-free conditions. NaHSO4.SiO2 can be recovered and re-used up to ten times by simple washing with diethyl ether after each use and activated in an oven at 120°C for 1 h, thus rendering the process more economical.
BF3-mediated additions of organolithiums to ketimines: X-ray crystal structures of BF3-ketimine complexes
Ma, Yun,Lobkovsky, Emil,Collum, David B.
, p. 2335 - 2337 (2007/10/03)
(Chemical Equation Presented) Additions of lithium acetylides and n-BuLi to N-alkyl ketimines mediated by BF3-Et2O in THF afford hindered tert-alkylamines in moderate to good yields. Stereochemical results and crystal structures of t
Lithium Diisopropylamide-Mediated Lithiations of Imines: Insights into Highly Structure-Dependent Rates and Selectivities
Liao, Songping,Collum, David B.
, p. 15114 - 15127 (2007/10/03)
Lithium diisopropylamide-mediated lithiations of N-alkyl ketimines derived from cyclohexanones reveal that simple substitutions on the N-alkyl side chain and the 2-position of the cyclohexyl moiety afford a 60,000-fold range of rates. Detailed rate studie
An efficient, scaleable procedure for the conversion of esters to isoxazoles
Bunnelle,Singam,Narayanan,Bradshaw,Liou
, p. 439 - 442 (2007/10/03)
A concise, regiocontrolled route to isoxazoles, based on the condensation of an ester with a metallated imine, has been developed. The intermediate vinylogous amides react smoothly with hydroxylamine to provide, after dehydration, substituted isoxazoles. The method has been used for the multi-kilo scale preparation of ABT-418, a novel cholinergic channel activator.
Novel routes to indoles, indolines, quinolines and tetrahydroquinolines from N-(cyclohexylidene)amines
De Kimpe, Norbert,Keppens, Marian
, p. 3705 - 3718 (2007/10/03)
Cyclohexanones have been converted into a variety of bicyclic azaheterocycles of different oxidation level via a sequence of reactions involving (a) imination, (b) α-alkylation with N,N-disilyl-protected ω-bromoamines, (c) transimination, (d) α-chlorination of the resulting bicyclic imines and (e) dehydrochlorination and/or dehydrogenation. Appropriate choice of the reaction conditions selectively led to reactions to indoles, 7-chloroindoles, 7-chloroindolines, 4,5,6,7-tetrahydroindoles, 8-chloro-1,2,3,4-tetrahydroquinolines, 8-chloroquinolines or quinolines.
An apparatus for the efficient removal of H2O from reaction mixtures
Barta,Paulvannan,Schwarz,Stille
, p. 583 - 590 (2007/10/02)
An apparatus has been designed that facilitates the azeotropic removal of H2O from a reaction mixture. Representative condensation reactions in which this apparatus was used include acetal, imine, and enamine formation.
Formation of 1,2,3,4-Tetrahydro-2-pyridones by Aza-Annulation of Imines with Acrylate Derivatives
Paulvannan, K.,Stille, John R.
, p. 5319 - 5328 (2007/10/02)
The aza-annulation of imines with activated acrylate derivatives was studied as a means of preparing the corresponding 1,2,3,4-tetrahydro-2-pyridones.Through the use of reagents known to facilitate the formation of amide bonds from carboxylic acids, several methods of activating the acrylate species were compared.The acrylate derivatives studied were acryloyl chloride and acrylic anhydride as well as acrylic acid activated by reaction with EtO2CCl, (PhO)2P(O)N3, or MCPI.Optimum annulation was obtained with imines derived from cyclohexanone to produce octahydro-2-quinolone products.The N-isobutylimine prepared from cyclopentanone also produced selective ring annulation to efficiently produce the corresponding bicyclic product, but the reaction with the imine of n-butanal produced lower yields of cyclic product.Ring formation was relatively unaffected by substituents at the α-position of the acrylate derivative, demonstrated by the use of methacrylate, but β-substituents hindered the annulation process and, in turn, increased the amounts of byproduct resulting from only N-acylation of the imine.Increasing the steric bulk of the imine alkyl substituent produced the opposite effect; the relative amount of N-acylation compared to complete aza-annulation was diminished as the size of the substituent was increased.Mechanistic features of the reaction are discussed in terms of product distribution and competition experiments.
