54311-89-6Relevant academic research and scientific papers
'Counter-intuitive' regioselectivity, subtle steric and solvation effects in lithiation of cyclic tertiary aralkylamines
Kessar, Satinder V.,Singh, Paramjit,Singh, Kamal Nain,Venugopalan,Kaur, Amarjit,Mahendru, Manu,Kapoor, Rajiv
, p. 6753 - 6755 (2005)
Lithiation of a series of cyclic aralkyl tertiary amines with sec-BuLi in various solvents has been studied. There is a subtle sensitivity to steric factors and lithium coordinating solvents/additives have an adverse effect. ortho-Lithiation is observed only in the case of an eight-membered cyclic amine and the ease of benzylic lithiation with respect to nitrogen is in the surprising order γ > β ? α, δ. These observations are discussed in the context of nitrogen coordination promoted lithiation.
An Improved Stereocontrolled Access Route to Piperidine or Azepane β-Amino Esters and Azabicyclic β- and γ-Lactams; Synthesis of Novel Functionalized Azaheterocyles
Ouchakour, Lamiaa,Nonn, Melinda,Remete, Attila M.,Kiss, Loránd
, p. 3874 - 3885 (2021/06/16)
An improved, efficient synthesis of some functionalized saturated azaheterocycles has been accomplished by controlled functionalization of various readily available cyclic compounds containing ring C=C bond. The stereocontrolled synthetic concept was based on the oxidative ring cleavage of various unsaturated scaffolds across ozonolysis followed by ring closing with double reductive amination with primary alkylamines or fluorinated alkylamines. The protocol provided versatile azaheterocyclic derivatives with a piperidine or azepane framework.
A de novo synthetic method to the access of N-substituted benzazepines
Ouchakour, Lamiaa,Nonn, Melinda,D'hooghe, Matthias,Kiss, Loránd
supporting information, (2020/02/04)
A novel, convenient procedure has been described for the construction of fluorine-containing benzazepines. The synthetic protocol starting from readily available dihydronaphthalene regioisomers is based on oxidative ring olefin bond cleavage followed by r
Facile and simple synthesis of N -alkyl and N -aryl 2-benzazepines by nucleophilic heteroannulation
Srinivasan,Rajashekar,Shyamapada,Syam Kumar
, p. 3112 - 3121 (2015/10/12)
An efficient and practical synthesis of N-alkyl and N-aryl 2-benzazepine has been developed. The key steps involved in the synthesis were palladium-mediated Heck reaction followed by aza heterocyclic ring construction by nucleophilic heteroannulation. This four-step sequence synthetic protocol gave moderate to good yields for a wide range of substrates. Subsequently, functionalization of the synthesized compound was carried out under Heck and Suzuki reaction conditions.
