13683-43-7Relevant articles and documents
Oxidative Rearrangement of Primary Amines Using PhI(OAc)2 and Cs2CO3
Yamakoshi, Wataru,Arisawa, Mitsuhiro,Murai, Kenichi
supporting information, (2019/05/08)
An oxidative rearrangement of primary amines mediated by a hypervalent iodine(III) reagent is herein reported. The combination of PhI(OAc)2 and Cs2CO3 proves highly efficient at inducing the direct 1,2-C to N migration of primary amines, which can be applied to the preparation of both acyclic and cyclic amines. A mechanistic study shows that the rearrangement proceeds via a concerted mechanism.
Modular synthesis of indoles from imines and o-dihaloarenes or o-chlorosulfonates by a Pd-catalyzed cascade process
Barluenga, Jose,Jimenez-Aquino, Agustin,Aznar, Fernando,Valdes, Carlos
supporting information; experimental part, p. 4031 - 4041 (2009/09/04)
A detailed study of the scope of a new Pd-catalyzed synthesis of indolesfrom 1,2-dihaloarenes and o-halobenzene sulfonates and imines is descri bed. The cascade reaction comprises an imine a-arylation ollowed by an intramolecular C-N bond-forming reaction promoted by the same Pd catalyst. The reaction with 1,2-dibromobenzene shows wide scope and allows the introduction of aryl, alkyl, and vinyl substituents at different positions of the five-membered ring of the indole. The regioselective synthesis of indoles substituted in the six-membered ring can be carried out by employing o-dihalobenzene derivatives with two different halogens, taking advantage of the different reactivities of I, Br, and Cl in oxidative addition reactions. This paper also introduces a method for the efficient cleavage of the N-t-butyl group, thus allowing for the preparation of N-H indoles through the same methodology. Finally, the reaction with o-halosulfonates has been studied. The best substrates are o-chlorononaflates, which lead to indoles in very high yield. The reaction is particularlyappropriate for the synthesis of the challenging 6-substituted indoles. In view of the availability of o-chlorophenols, which are direct precur sors of the chlorononaflates, this reaction represents an efficient entry into indoles substituted in the six-membered ring. The concept is illustrated by the preparation of a 4,6-disubstituted indole from naturally occurring anethole.
In vitro antifungal activity of new series of homoallylamines and related compounds with inhibitory properties of the synthesis of fungal cell wall polymers
Vargas M., Leonor Y.,Castelli, Maria V.,Kouznetsov, Vladimir V.,Urbina G., Juan M.,Lopez, Silvia N.,Sortino, Maximiliano,Enriz, Ricardo D.,Ribas, Juan C.,Zacchino, Susana
, p. 1531 - 1550 (2007/10/03)
The synthesis, in vitro antifungal evaluation and SAR studies of 101 compounds of the 4-aryl-, 4-alkyl-, 4-pyridyl or -quinolinyl-4-N-arylamino-1-butenes series and related compounds, are reported here. Active structures showed to inhibit (1,3)-β-D-glucan and mainly chitin synthases, enzymes that catalyze the synthesis of the major fungal cell wall polymers.