Synthesis of substituted N-arylpiperidines via organobismuth derivatives
The synthesis of N-arylpiperidines functionalized both on the aromatic and piperidine ring was performed using conveniently substituted triarylbismuthine derivatives as arylating agents. This method is, in particular, indicated to arylate the nitrogen atom of a secondary amine with a phenyl ring bearing electron-withdrawing groups in the m-position.
(l)-Proline-catalysed novel tandem reactions of 1-substituted piperidin-4-ones with (E)-4-arylbut-3-en-2-ones: N-substituent mediated product selectivity and synthesis of novel nitrogen heterocycles
(l)-Proline-catalysed reaction of 1-alkyl/aralkylpiperidin-4-ones with (E)-4-arylbut-3-en-2-ones furnishes novel isoquinoline derivatives, with two or three rings, in good yields via tandem Robinson annulation-Michael addition(s) sequences, while the reaction of 1-arylpiperidin-4-ones with (E)-4-arylbut-3-en-2-ones affords 3-azabicyclo[3.3.1]nonan-9-ones via a tandem Michael addition-aldol reaction sequence.
Srinivasan, Murugesan,Perumal, Subbu
p. 2865 - 2874
(2007/10/03)
Some observations relating to the use of 1-aryl-4-alkoxypiperidin-4-yl groups for the protection of the 2′-hydroxy functions in the chemical synthesis of oligoribonucleotides
The comparative rates of acid-catalysed removal often 1-aryl-4-methoxypiperidin-4-yl 8 (R = Me) [including the previously reported Ctmp 5 and Fpmp 6] protecting groups for the 2′-hydroxy functions in oligoribonucleotide synthesis are discussed. These studies have led to the development of the 1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl (Cpep) protecting group 8 (R = Et, R1 = R2 = H, R3 = Cl) which is both more stable than the Ctmp and Fpmp groups at pH 0.5 and more labile at pH 3.75. The influence of the ribonucleoside aglycone on the stability of the 2′-O-Fpmp and 2′-O-Ctmp protecting groups both at low and high pH is examined. The Royal Society of Chemistry 2000.
Lloyd, Wayne,Reese, Colin B.,Song, Quanlai,Vandersteen, Anthony M.,Visintin, Cristina,Zhang, Pei-Zhou
p. 165 - 176
(2007/10/03)
A convenient synthesis to N-aryl-substituted 4-piperidones
(matrix presented) A general and efficient procedure for the synthesis of N-aryl-substituted 4-piperidones was developed. The general methodology was applied to the synthesis of several different N-aryl-4-piperidones utilizing an expedient two-step proces
Tortolani, David R.,Poss, Michael A.
p. 1261 - 1262
(2008/02/09)
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