179242-29-6Relevant articles and documents
A direct synthesis of substituted α-allenic carboxanilides from allenyllithium reagents
Audin,Drut-Grevoz,Paris
, p. 1139 - 1145 (1993)
The metalation of various allenic hydrocarbons and the subsequent reaction of the lithioderivatives with phenyl isocyanates as a synthetic route to α - allenyl carboxanilides is described. The best results were obtained with 3,3-disubstituted propadiene and 3,3,1- trisubstituted propadiene.
Synthesis of Exo- and Endocyclic Enamides Through Copper-Catalyzed Regioselective Intramolecular N-Halovinylation
Bergeron, Jodrey,Daoust, Benoit,Gilbert, Nicolas,Lambolez, Pierre,Ricard, Simon
supporting information, (2020/05/04)
Cross-couplings between amides and 1,2-dihaloalkenes are an efficient and straightforward way to access β-haloenamides which, in turn, can be functionalized into complex, stereodefined enamide motifs. However, the intramolecular version of these cross-couplings, leading to cyclic β-haloenamides, has not been formally studied. In this paper, we report an investigation of factors affecting the efficiency of the reaction and its selectivity between potential exo and endo cyclization products. We demonstrate that exo/endo selectivity is largely determined by ring strain, whether it arises from the size of the resulting ring or from the structure of the starting compound, but that selectivity can also be modulated by varying reaction conditions. Finally, we show that resulting β-haloenamides readily undergo transition metal-catalyzed reactions, making this sequence a viable way to access highly functionalized cyclic enamides.
Cycloadditions. 24. Synthesis and reactions of sec. N-aryl-2,3-butadienamides
Himbert, Gerhard,Fink, Dieter
, p. 355 - 362 (2007/10/03)
The reaction of aryl isocyanates (1) with allenyl magnesium bromide (2) furnishes the sec. N-aryl-3-butynamides (4), which tend to tautomerize to the 2,3-butadienamides (5). Further heating of 5a-f (bearing benzoid nuclei) leads to decompositon, only 5g (bearing the naphthyl group) undergoes the expected intramolecular Diels-Alder (IMDA) reaction, leading to the benzo-tricycle (7g). By reaction of a second molecule isocyanate 1 the carbamoylation of the NH moiety of 5a, c and of 3g and 4g, resp. takes place. The thereby formed N-aryl-N-butadienoyl ureas (9) either cyclize to furnish the the N-carbamoyl-2-quinolones (10) or undergo the IMDA-reaction leading to the tricyclic compounds (11). The N-butadienoyl-N-(1-naphthyl)ureas (12) only furnish the IMDA-benzo-tricycles (13). Johann Ambrosius Barth 1996.
