- Remote C(sp3)-H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate
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This letter describes the development of a method for selective remote C(sp3)-H oxygenation of protonated aliphatic amines using aqueous potassium persulfate. Protonation serves to deactivate the proximal C(sp3)-H bonds of the amine substrates and also renders the amines soluble in the aqueous medium. These reactions proceed under relatively mild conditions (within 2 h at 80 °C with amine as limiting reagent) and do not require a transition metal catalyst. This method is applicable to a variety of types of C(sp3)-H bonds, including 3°, 2°, and benzylic C-H sites in primary, secondary, and tertiary amine substrates.
- Lee, Melissa,Sanford, Melanie S.
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p. 572 - 575
(2017/02/10)
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- Synthesis and in vitro and in vivo evaluation of18F-labeled positron emission tomography (PET) ligands for imaging the vesicular acetylcholine transporter
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A new class of vesicular acetylcholine transporter inhibitor that incorporates a carbonyl group into the benzovesamicol structure was synthesized, and analogues were evaluated in vitro. (±)-trans-2-Hydroxy-3- (4-(4-[18F]fluorobenzoyl)piperidino)tetralin (9e) has Ki values of 2.70 nM for VAChT, 191 nM for σ1 and 251 nM for σ2. The racemic precursor (9d) was resolved via chiral HPLC, and (±)-[18F]9e,(-)-[18F]9e, and (+)-[ 18F]9e were respectively radiolabeled via microwave irradiation of the appropriate precursors with [18F]/F- and Kryptofix/K 2CO3 in DMSO with radiochemical yields of ~50-60% and specific activities of >2000 mCi/μmol. (-)-[18F]9e uptake in rat brain was consistent with in vivo selectivity for the VAChT with an initial uptake of 0.911 %ID/g in rat striatum and a striatum/cerebellum ratio of 1.88 at 30 min postinjection (p.i.). MicroPET imaging of macaques demonstrated a 2.1 ratio of (-)-[18F]9e in putamen versus cerebellum at 2 h p.i. (-)-[18F]9e has potential to be a PET tracer for clinical imaging of the VAChT.
- Tu, Zhude,Efange, Simon M. N.,Xu, Jinbin,Li, Shihong,Jones, Lynne A.,Parsons, Stanley M.,Mach, Robert H.
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experimental part
p. 1358 - 1369
(2009/12/26)
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- Synthesis of diarylazepan-4-ones
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Synthesis of several 3,3-diarylazepan-4-ones and 5,5-diarylazepan-4-ones has been established starting from two tetrasubstituted olefins, which is derived from commercially available piperidine-3-carboxylic acid ethyl ester and piperidine-4-carboxylic aci
- Chang, Meng-Yang,Kung, Yung-Hua,Ma, Chih-Chong
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p. 199 - 202
(2007/10/03)
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- CAN-mediated rearrangement of 4-benzhydrylidenepiperidines
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Several 1-substituted phenyl-(4-phenylpiperidin-4-yl)methanones are synthesized in modest overall yields starting from the reaction of different 1-substituted 4-benzhydrylidenepiperidines via CAN-mediated rearrangement. This facile strategy was also used to synthesize meperidine analog.
- Chang, Meng-Yang,Wu, Tsun-Cheng,Lin, Chun-Yu,Hung, Ching-Yi
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p. 8347 - 8350
(2007/10/03)
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