Synthesis of Piperazinones, Piperazines, Tetrahydropyrazines, and Dihydropyrazinones from Polymer-Supported Acyclic Intermediates via N-Alkyl- and N-Acyliminiums

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F12%3A33141476" target="_blank" >RIV/61989592:15310/12:33141476 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/ejoc.201200591" target="_blank" >http://dx.doi.org/10.1002/ejoc.201200591</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201200591" target="_blank" >10.1002/ejoc.201200591</a>

Result language
angličtina
Original language name
Synthesis of Piperazinones, Piperazines, Tetrahydropyrazines, and Dihydropyrazinones from Polymer-Supported Acyclic Intermediates via N-Alkyl- and N-Acyliminiums
Original language 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 targetcompounds 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. A
Czech name
—
Czech description
—

Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
—

Project
<a href="/en/project/ME09057" target="_blank" >ME09057: Research of new organic compounds with anticancer activity with use of combinatorial chemistry</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2012
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Similar results(10)