5176-20-5Relevant academic research and scientific papers
Solvolysis of syn- and anti-N-Chloro-1,4-dihydro-1,4-iminonaphthalenes
Durrant, Michael L.,Malpass, John R.
, p. 1028 - 1030 (1981)
The configuration of chlorine determines the course of methanolysis of the title compounds; new structures are assigned to the reaction products and the rates of reaction of the anti-N-chloroamines are shown to vary according to the ability of the substituents in the benzo-ring to encourage benzo-participation.
Solvolysis of N-Chloro-1,4-dihydro-1,4-iminonaphthalenes (7-Azabenzonorbornadienes); Dependence of the Rearrangement Pathway on the Configuration at Nitrogen
Durrant, Michael L.,Malpass, John R.
, p. 7063 - 7076 (1995)
N-Chloro- derivatives of the 1,4-dihydro-1,4-iminonaphthalene (7-azabenzonorbornadiene) ring system undergo silver (I)-assisted rearrangement with participation of etheno- (syn-chloro- series) or benzo- (anti-chloro- series) ?-electrons.The high barriers to inversion at nitrogen together with some control over the ratio of invertomers allow observation of a different reaction pathway for each invertomer when reactions are performed at low temperatures; approaches which allow selection of the benzo- participation route (giving 6,7-benzo-derivatives of the 1-azabicyclohept-3-ene ring system) are described.
Azabicycloalkenes as synthetic intermediates - Synthesis of azabicyclo[x.3.0]alkane scaffolds
Buchert, Marina,Meinke, Sebastian,Prenzel, Alexander H. G. P.,Deppermann, Nina,Maison, Wolfgang
, p. 5553 - 5556 (2006)
A general method to synthesize functionalized azabicyclo[X.3.0]alkane scaffolds 5 is reported. Key intermediates are azabicycloalkenes such as 1 and 2, which are acylated with unsaturated carboxylic acids and subsequently submitted to tandem olefin metathesis. The resulting bicyclic heterocycles are versatile intermediates for different dipeptide mimetics and can be used as intermediates for natural products with indolizidine scaffolds or analogues thereof.
Azabicycloalkenes as synthetic intermediates: Application to the preparation of diazabicycloalkane scaffolds
Prenzel, Alexander H. G. P.,Deppermann, Nina,Maison, Wolfgang
, p. 1681 - 1684 (2007/10/03)
A general method to synthesize bicyclic dipeptide mimetics is reported. Key intermediates are azabicycloalkenes 9 and 17, which are prepared via Diels-Alder reactions and subsequent mild deprotection. These unsaturated bicyclic heterocycles are versatile
Preparation and Spectroscopic Studies of the 1,4-Dihydro-1,4-iminonaphthalene (7-Azabenzonorbornadiene) Ring System
Davies, John W.,Durrant, Michael L.,Walker, Matthew P.,Belkacemi, Djaballah,Malpass, John R.
, p. 861 - 884 (2007/10/02)
The synthesis of a range of N-alkyl 1,4-dihydro-1,4-iminonaphthalenes (7-azabenzonorbornadienes) and reduced derivatives is described together with 1,4-dihydro-1,4- and 9,10-dihydro-9,10- iminoanthracenes.VT NMR studies lead to unambiguous assignment of i
