2-AZABICYCLO[2.2.2]OCT-7-ENES. 1. Synthesis From Polysubstituted 1,2-Dihydropyridines

Mechanisms of Diels‐Alder reactions between pyridines and dienophiles: A DFT investigation

“…[7] Unfortunately, the incorporation of an acyl protecting group could weaken the nucleophilicity of dihydropyridines. [8] Martin et al [9] took highly substituted N-alkyl and aryl-1,2-dihydropyridines and electron-deficient alkenes to go through D-A reactions to yield unprecedented substitution isoquinuclidines products, which has good yield and higher stereoselectivities. To investigate the detailed mechanisms of these reactions, we carried out theoretical studies in the following parts.…”

Synthesis of Fluorinated 3,6-Dihydropyridines and 2-(Fluoromethyl)pyridines by Electrophilic Fluorination of 1,2-Dihydropyridines with Selectfluor®

“…Thus, isomerisation involving hydride transfer was shown to convert 1,2-dihydropyridines into their 1,4-isomers in the presence of the transition metal complex RhCl(PPh 3 ) 2 [ 33 ]. Polysubstituted 1,2-dihydropyridines have been found to undergo [4+2] cycloaddition as reactive dienes with maleic anhydride, dimethyl fumarate and methyl acrylate, leading to the formation of 2-azabicyclo[2.2.2]oct-7-enes [ 34 ]. The regiospecific 1,3-dipolar cycloaddition reaction of 1,2-dihydropyridines with cyanogen azide and per(poly)fluoroalkanesulfonyl azides has afforded corresponding 2,7-diazabicyclo[4.1.0]hept-4-enes and N -(1,2,3,6-tetrahydropyridylidene)fluoroalkanesulfonylamides [ 35 , 36 ].…”