Attributes | Values |
---|
rdf:type
| |
Description
| - Trisubstituted piperazinones, piperazines, tetrahydropyrazines, and dihydropyrazinones were prepared in a one-step procedure from easily accessible polymer-supported acyclic precursors containing either a masked aldehyde or ketone group. Acid-mediated unmasking of the aldehyde triggered cyclic iminium formation followed by reduction with triethylsilane present in the cleavage cocktail. The effect of the substituent at the iminium-forming nitrogen was evaluated: whereas complete conversion to the target compounds was observed with N-alkyl, aryl, and phenylsulfonamido derivatives, the N-acyl compound suffered from a partial reduction of the aldehyde to an alcohol. Similarly, ketones readily provided cyclic iminiums with N-alkyl compounds, whereas their cyclization with N-acyl precursors proceeded unwillingly. Interestingly, cleavage of the resin-bound acyclic precursor at 60 °C in the presence of triethylsilane resulted in the decomposition of the amide bond and formation of a lactone. An analogous synthetic route was also successfully used for the preparation of piperazines and tested as an alternative route for the synthesis of diazepanones.
- Trisubstituted piperazinones, piperazines, tetrahydropyrazines, and dihydropyrazinones were prepared in a one-step procedure from easily accessible polymer-supported acyclic precursors containing either a masked aldehyde or ketone group. Acid-mediated unmasking of the aldehyde triggered cyclic iminium formation followed by reduction with triethylsilane present in the cleavage cocktail. The effect of the substituent at the iminium-forming nitrogen was evaluated: whereas complete conversion to the target compounds was observed with N-alkyl, aryl, and phenylsulfonamido derivatives, the N-acyl compound suffered from a partial reduction of the aldehyde to an alcohol. Similarly, ketones readily provided cyclic iminiums with N-alkyl compounds, whereas their cyclization with N-acyl precursors proceeded unwillingly. Interestingly, cleavage of the resin-bound acyclic precursor at 60 °C in the presence of triethylsilane resulted in the decomposition of the amide bond and formation of a lactone. An analogous synthetic route was also successfully used for the preparation of piperazines and tested as an alternative route for the synthesis of diazepanones. (en)
|
Title
| - Synthesis of Piperazinones, Piperazines, Tetrahydropyrazines, and Dihydropyrazinones from Polymer-Supported Acyclic Intermediates via N-Alkyl- and N-Acyliminiums
- Synthesis of Piperazinones, Piperazines, Tetrahydropyrazines, and Dihydropyrazinones from Polymer-Supported Acyclic Intermediates via N-Alkyl- and N-Acyliminiums (en)
|
skos:prefLabel
| - Synthesis of Piperazinones, Piperazines, Tetrahydropyrazines, and Dihydropyrazinones from Polymer-Supported Acyclic Intermediates via N-Alkyl- and N-Acyliminiums
- Synthesis of Piperazinones, Piperazines, Tetrahydropyrazines, and Dihydropyrazinones from Polymer-Supported Acyclic Intermediates via N-Alkyl- and N-Acyliminiums (en)
|
skos:notation
| - RIV/61989592:15310/12:33141476!RIV13-MSM-15310___
|
http://linked.open...avai/predkladatel
| |
http://linked.open...avai/riv/aktivita
| |
http://linked.open...avai/riv/aktivity
| |
http://linked.open...iv/cisloPeriodika
| |
http://linked.open...vai/riv/dodaniDat
| |
http://linked.open...aciTvurceVysledku
| |
http://linked.open.../riv/druhVysledku
| |
http://linked.open...iv/duvernostUdaju
| |
http://linked.open...titaPredkladatele
| |
http://linked.open...dnocenehoVysledku
| |
http://linked.open...ai/riv/idVysledku
| - RIV/61989592:15310/12:33141476
|
http://linked.open...riv/jazykVysledku
| |
http://linked.open.../riv/klicovaSlova
| - Piperazinones, Cyclization, Piperazines, Solid-phase synthesis, Iminiums, Heterocycles (en)
|
http://linked.open.../riv/klicoveSlovo
| |
http://linked.open...odStatuVydavatele
| - DE - Spolková republika Německo
|
http://linked.open...ontrolniKodProRIV
| |
http://linked.open...i/riv/nazevZdroje
| - European Journal of Organic Chemistry
|
http://linked.open...in/vavai/riv/obor
| |
http://linked.open...ichTvurcuVysledku
| |
http://linked.open...cetTvurcuVysledku
| |
http://linked.open...vavai/riv/projekt
| |
http://linked.open...UplatneniVysledku
| |
http://linked.open...v/svazekPeriodika
| |
http://linked.open...iv/tvurceVysledku
| - Krchňák, Viktor
- Vaňková, Barbora
- Brulíková, Lucie
- Wu, Boyuan
|
http://linked.open...ain/vavai/riv/wos
| |
issn
| |
number of pages
| |
http://bibframe.org/vocab/doi
| |
http://localhost/t...ganizacniJednotka
| |
is http://linked.open...avai/riv/vysledek
of | |