Synthesis of 3-Sulfonylamino Quinolines from 1-(2-Aminophenyl) Propargyl Alcohols through a Ag(I)-Catalyzed Hydroamination, (2 + 3) Cycloaddition, and an Unusual Strain-Driven Ring Expansion
We describe herein a silver-catalyzed conversion of 1-(2-aminophenyl)-propargyl alcohols to 4-substituted 3-tosylaminoquinolines using TsN3 as an amino surrogate. Controlled reactions reveal the pathway consisting of Ag(I)-catalyzed 5-exo-dig cyclization, catalyst-free (2 + 3) cycloaddition, and ring-expansive rearrangement via nitrogen expulsion. As a support study, we show that the cyclic enamines
In vitro antifungal activity of new series of homoallylamines and related compounds with inhibitory properties of the synthesis of fungal cell wall polymers
作者:Leonor Y Vargas M、Marı́a V Castelli、Vladimir V Kouznetsov、Juan M Urbina G、Silvia N López、Maximiliano Sortino、Ricardo D Enriz、Juan C Ribas、Susana Zacchino
DOI:10.1016/s0968-0896(02)00605-3
日期:2003.4
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 relatedcompounds, are reported here. Active structures showed to inhibit (1,3)-beta-D-glucan and mainly chitin synthases, enzymes that catalyze the synthesis of the major fungal cell wall polymers.
4-Methyl-3,4-dihydrospiro[cycloheptane-1′,2(1<i>H</i>)-quinoline] and 4-methyl-3,4-dihydrospiro[cyclooctane-1′,2(1<i>H</i>)-quinoline]. synthesis of derivatives and chemical transformations
New derivatives of 3,4-dihydrospiro[cycloalkane-1′,2(1H)-quinolines] were obtained from cycloheptanone and cyclooctanone via facile three steps hetero spiro annulation process. Their nitro derivatives were prepared through electrophilic substitution reactions.