1101197-07-2Relevant academic research and scientific papers
Borane-Catalyzed Reduction of Pyridines via a Hydroboration/Hydrogenation Cascade
Yang, Zhao-Ying,Luo, Heng,Zhang, Ming,Wang, Xiao-Chen
, p. 10824 - 10829 (2021/09/08)
We have developed a method for a B(C6F5)3-catalyzed hydroboration/hydrogenation cascade reduction of pyridines. The method was particularly effective for 2,3-disubstituted pyridines, which generated piperidines in high yields with high cis selectivity. Mechanistic studies indicated that the pyridine substrates and the piperidine products sequentially acted as bases in cooperation with B(C6F5)3to split H2. The broad functional group tolerance of the method allowed its use for the synthesis of some biologically active molecules.
Iterative direct C(sp3)-H functionalization of amines: diastereoselective divergent syntheses of ??,α′-disubstituted alicyclic amines
Mahato, Sujit,Jana, Chandan K.
, p. 1655 - 1660 (2017/02/23)
A novel iterative C(sp3)-H oxygenation/C-C bond formation strategy, which avoids repetitive N-protection/-deprotection steps, was developed for direct α,α′-difunctionalization of alicyclic amines. The method is highly efficient and stereoselective in producing syn-α,α′-disubstituted aliphatic N-heterocycles. Synthetic potential and practicability of the method was demonstrated by an easy and straightforward synthesis of neuroactive alkaloid nor-lobelane and its derivatives.
Synthesis and evaluation of a series of homologues of lobelane at the vesicular monoamine transporter-2
Zheng, Guangrong,Dwoskin, Linda P.,Deaciuc, Agripina G.,Crooks, Peter A.
scheme or table, p. 6509 - 6512 (2009/10/01)
A series of lobelane homologues has been synthesized and evaluated for their [3H]DTBZ binding affinity at the vesicular monoamine transporter-2 (VMAT2). The structure-activity relationships (SAR) indicate that for retention of binding affinity at VMAT2, the lengths of the methylene linkers should be no shorter than one methylene unit at C-6 of the piperidine ring, and no shorter than two methylene units at C-2 of the piperidine ring. These results indicate that the intramolecular distances between the piperidine ring and two phenyl rings in lobelane analogues are an important criterion for retention of high affinity at VMAT2.
