31930-96-8Relevant academic research and scientific papers
Structural Characterization of 11-Ethyl-6,11-Dihydro-5H-Dibenzo[b,e]Azepine
Delgado,Osal,Mora,González,Palma,Bahsas
, p. 1210 - 1214 (2018/12/10)
The title compound C16H17N, a potential pharmaceutical agent, crystallizes in the monoclinic P21/n space group with unit cell parameters a = 9.911(7) ?, b = 5.542(3) ?, c = 23.245(16) ?, β = 96.25(2)°. The dibenzazepine ri
Highly efficient and regioselective allylic amination of allylic alcohols catalyzed by [Mo3PdS4] cluster
Tao, Yinsong,Zhou, Yuhan,Qu, Jingping,Hidai, Masanobu
experimental part, p. 1982 - 1984 (2010/06/21)
A highly efficient and regioselective allylation reaction of amines with allylic alcohols under mild conditions catalyzed by the cubane-type sulfido cluster [(Cp*Mo)3S4Pd(dba)][PF6] with H3BO3 as an additive has been developed. A variety of amines and allylic alcohols are investigated, and in the case of allylic alcohols bearing substituents at either α- or γ-position only linear allylic amination products are obtained.
Highly efficient and regioselective allylation with allylic alcohols catalyzed by [Mo3S4Pd(η3-allyl)] clusters
Tao, Yinsong,Wang, Bo,Wang, Baomin,Qu, Lihong,Qu, Jingping
experimental part, p. 2726 - 2729 (2010/08/06)
(Figure presented) A highly efficient and regioselective allylation reaction of amines and active methylene compounds directly using allylic alcohols under mild conditions catalyzed by the novel cubane-type sulfido [(CpMo)3(μ3-S)4Pd(η3-allyl)] [PF6]2 clusters has been developed. A variety of allylic alcohols and nucleophiles including amines and active methylene compounds are investigated, and in the case of allylic alcohols bearing substituents at either the α- or γ-position only linear products are obtained.
Synthesis, structural elucidation and in vitro antiparasitic activity against Trypanosoma cruzi and Leishmania chagasi parasites of novel tetrahydro-1-benzazepine derivatives
Gomez-Ayala, Sandra,Castrillon, Julian A.,Palma, Alirio,Leal, Sandra M.,Escobar, Patricia,Bahsas, Ali
experimental part, p. 4721 - 4739 (2010/08/22)
Forty six new 1,4-epoxy-2-exo-aryl- and cis-2-aryl-4-hydroxytetrahydro-1- benzazepine derivatives were synthesized and fully characterized. All compounds were tested in vitro against both Trypanosoma cruzi and Leishmania chagasi parasites and also for cyt
Sequential amino-Claisen rearrangement/intramolecular 1,3-dipolar cycloaddition/reductive cleavage approach to the stereoselective synthesis of cis-4-hydroxy-2-aryl-2,3,4,5-tetrahydro-1(1H)-benzazepines
Ayala, Sandra Liliana Gómez,Stashenko, Elena,Palma, Alirio,Bahsas, Alí,Amaro-Luis, Juan Manuel
, p. 2275 - 2277 (2007/10/03)
A novel stereoselective synthesis of cis-2-aryl-4-hydroxy-2,3,4,5- tetrahydro-1-benzazepines from N-allylanilines utilizing aromatic amino-Claisen rearrangement and intramolecular 1,3-dipolar cycloaddition methodologies is described. This sequence involve
New and efficient synthesis of 6,11-dihydro-11-ethyl-5H-dibenz[b,e]azepine derivatives starting from N-benzylanilines via amino-Claisen and Friedel-Crafts methodologies
Palma, Alirio,Barajas, Jacqueline Jaimes,Kouznetsov, Vladimir V.,Stashenko, Elena,Bahsas, Ali,Amaro-Luis, Juan
, p. 2721 - 2724 (2007/10/03)
New and efficient synthesis of 6,11-dihydro-11-ethyl-5H-dibenz[b,e]azepine derivatives, using the key steps of BF3·OEt 2-catalyzed aromatic amino-Claisen rearrangement and the intramolecular alkene Friedel-Crafts alkylation, is reported.
Ruthenium-Catalyzed Chemoselective N-Allyl Cleavage: Novel Grubbs Carbene Mediated Deprotection of Allylic Amines
Alcaide, Benito,Almendros, Pedro,Alonso, Jose M.
, p. 5793 - 5799 (2007/10/03)
A novel application of the Grubbs carbene complex has been discovered. The first examples of the catalytic deprotection of allylic amines with reagents other than palladium catalysts have been achieved through Grubbs carbene mediated reaction. Significantly, the catalytic system directs the reaction toward the selective deprotection of allylic amines (secondary as well as tertiary) in the presence of allylic ethers. A variety of substrates, including enantiomerically pure multifunctional piperidines, are also usable. The new method is more convenient, chemoselective, and operationally simple than the palladium-catalyzed method. The current mechanistic hypothesis invokes a nitrogen-assisted ruthenium-catalyzed isomerization, followed by hydrolysis of the enamine intermediate. We believe that the reactive species involved in the reaction may be an Ru-H species rather than the Grubbs carbene itself. Thus, the isomerization may occur according to the hydride mechanism. The synthetic utility of this ruthenium-catalyzed allyl cleavage is illustrated by the preparation of indolizidine-type alkaloids.
Highly Coordinated Tin Hydrides: A Novel Synthesis of Tertiary Amines via Hydrostannation of Imines
Kawakami, Takayo,Sugimoto, Takayuki,Shibata, Ikuya,Baba, Akio,Matsuda, Haruo,Sonoda, Noboru
, p. 2677 - 2682 (2007/10/02)
The highly coordinated tin hydride, Bu2SnClH-HMPA (B), is shown to be an effective agent for the reduction of imines.The subsequent alkylation of the resulting intermediate tin amides permitted the preparation of a series of tertiary amines in a one-pot procedure.The spectral identification of the novel tin hydrides, B and Bu2SnClH-Bu4NF, was accomplished by 1H, 13C, and 119Sn NMR and FT-IR studies.
Lewis Acid-Promoted 3-Aza-Cope Rearrangement of N-Alkyl-N-allylanilines
Beholz, Lars G.,Stille, John R.
, p. 5095 - 5100 (2007/10/02)
The 3-aza-Cope rearrangement of N-alkyl-N-alkylaniline substrates, which required 250 deg C to proceed thermally, was promoted by Lewis acid reagents at 111-140 deg C.Systematic studies of this reaction were performed to examine a number of reaction variables such as concentration, the stoichiometry of the Lewis acid with the substrate, the optimum temperature for rearrangement, and the type of Lewis acid reagent.Of the many Lewis acids investigated, ZnCl2 (140 deg C) and Et2O*BF3 (111 deg C) were the most generally successful reagents for promoting the aromatic 3-aza-Cope rearrangement.With respect to substrate variation, the presence of a methoxy substituent para to the N-allyl group slowed the reaction slightly, while a meta substituent accelerated the rate of rearrangement and produced moderate site selectivity on the aromatic ring.Lewis acid-promoted rearrangement of an unsymmetrically substituted allyl moiety resulted in sigmatropic rearrangement to give the 1-hexen-3-yl substituent on the aromatic ring.Overall, both ZnCl2 and Et2O*BF3 were shown to efficiently accelerate the regiospecific 3-aza-Cope rearrangement of N-alkyl-N-allylanilines for the purpose of forming a carbon-carbon bond between a secondary alkyl substituent and an aromatic ring.
The Pyrolysis of N-Allyl Compounds: Free-radical and Retro-ene Mechanisms
Cadogan, J. I. G.,Hickson, Clare L.,McNab, Hamish
, p. 2247 - 2273 (2007/10/02)
Flash vacuum pyrolysis of N-alkyl-N-allylanilines gives imines by free radical cleavage of the allyl group followed by loss of an atom (or group of atoms) from the α-carbon atom of the alkyl group.The corresponding N-propargyl derivatives also give imines on pyrolysis, but the mechanism is a concerted retro-ene process which may lead to different products from the corresponding N-allyl compound.N-Allyl-N,N-dialkylamines also decompose thermally by a retro-ene process
