83928-76-1Relevant academic research and scientific papers
Late Stage Functionalization of Secondary Amines via a Cobalt-Catalyzed Electrophilic Amination of Organozinc Reagents
Gra?l, Simon,Chen, Yi-Hung,Hamze, Clémence,Tüllmann, Carl Phillip,Knochel, Paul
, p. 494 - 497 (2019/01/14)
A general preparation of polyfunctional hydroxylamine benzoates from the corresponding secondary amines is reported. This convenient synthesis allows the setup of a late-stage functionalization of various secondary amines, including pharmaceuticals and peptidic derivatives. Thus, a cross-coupling of hydroxylamine benzoates with various alkyl-, aryl-, and heteroaryl-zinc chlorides in the presence of 5 mol % CoCl2 (25 °C, 2 h) provides a range of polyfunctional tertiary amines. This method was used to prepare penfluridol and gepirone.
The design and preparation of metabolically protected new arylpiperazine 5-HT1A ligands
Tandon, Manish,O'Donnell, Mary-Margaret,Porte, Alex,Vensel, David,Yang, Donglai,Palma, Rocio,Beresford, Alan,Ashwell, Mark A.
, p. 1709 - 1712 (2007/10/03)
New arylpiperazines related to buspirone, gepirone and NAN-190 were designed and screened in silico for their 5-HT1A affinity and potential sites of metabolism by human cytochrome P450 (CYP3A4). Modifications to these structures were assessed in silico for their influence on both 5HT 1A affinity and metabolism. Selected new molecules were synthesized and purified in a parallel chemistry approach to determine structure activity relationships (SARs). The resulting molecules were assessed in vitro for their 5HT1A affinity and half-life in a heterologously expressed human CYP3A4 assay. Molecular features responsible for 5-HT1A affinity and CYP3A4 stability are described.
Process for preparing certain azapirones
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, (2008/06/13)
An improved process for preparation of certain useful azapirones, e.g. buspirone, gepirone, tandospirone, etc., comprises the reaction of a novel spiroquaternary piperazinium hydroxide with an appropriate imide to form imidate salts which are then converted to the azapirone by heating. This process is suitable for large scale adaptation and has advantages in greater safety and efficiency.
PD(O)-CATALYSED SYHTHESIS OF BUSPIRONE AND GEPIRONE
Kuo, David L.
, p. 1463 - 1470 (2007/10/02)
A novel synthetic approach to buspirone and its analogue (gepirone) is described, in which 3 subunits, namely 2-(1-piperazinyl)pyrimidine, a bifunctional allylderivative, and an imide were efficiently assembled via a Pd(O)-catalysed amination-imidation sequence followed by a hydrogenation.
