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@article{1217978, author = {Herová, Dana and Pazdera, Pavel}, article_number = {4}, doi = {http://dx.doi.org/10.1007/s00706-014-1379-2}, keywords = {Aza-Michael addition; Catalysis; Metal catalysis; One-pot synthesis; Resin-supported metal ion}, language = {eng}, issn = {0026-9247}, journal = {Monatshefte für Chemie - Chemical Monthly}, title = {Efficient solid support catalyzed mono-aza-Michael addition reactions of piperazine}, volume = {146}, year = {2015} }
TY - JOUR ID - 1217978 AU - Herová, Dana - Pazdera, Pavel PY - 2015 TI - Efficient solid support catalyzed mono-aza-Michael addition reactions of piperazine JF - Monatshefte für Chemie - Chemical Monthly VL - 146 IS - 4 SP - 653-661 EP - 653-661 SN - 00269247 KW - Aza-Michael addition KW - Catalysis KW - Metal catalysis KW - One-pot synthesis KW - Resin-supported metal ion N2 - We report new methods for the efficient mono-aza-Michael additions of piperazine to compounds with activated multiple carbon–carbon bond (functional derivatives of acrylic, propiolic, and acetylenedicarboxylic acid). This method is based on the reaction of piperazine-1-ium cation with alkenes or alkynes substituted by EWGs under catalysis by various metal ions supported on weakly acidic cation-exchanger resin. Starting piperazine-1-ium cation is generated in situ in methanol solution by mixing of piperazine and piperazine-1,4-diium dichloride in various ratios. It was found that solid support metal catalysis afforded target products in very good yields in shortened reaction times. A new method of N-monosubstituted piperazine derivative preparation is very beneficial, because until now no one has come up with the idea to use for protection of the one nitrogen atom of the piperazine its simple protonation. Computer modeling of behavior of piperazine depending on the pH was carried out and according to the results, we concluded that the protonation of the nitrogen atom is the simplest, most effective, and most elegant method of preventing unwanted formation of 1,4-disubstituted product. Assumption was fully confirmed by number of syntheses. The main advantages of our syntheses are great simplicity, one-pot performance, use of non-toxic solvents only, mild reaction conditions, no generation of waste, short time of reactions, and high yields. ER -
HEROVÁ, Dana and Pavel PAZDERA. Efficient solid support catalyzed mono-aza-Michael addition reactions of piperazine. \textit{Monatshefte für Chemie - Chemical Monthly}. 2015, vol.~146, No~4, p.~653-661. ISSN~0026-9247. Available from: https://dx.doi.org/10.1007/s00706-014-1379-2.
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