103863-15-6Relevant articles and documents
Tuning Reactivity in Pd-catalysed C(sp3)-H Arylations via Directing Group Modifications and Solvent Selection
Coomber, Charlotte E.,Porter, Michael J.,Aliev, Abil E.,Smith, Peter D.,Sheppard, Tom D.
, p. 5105 - 5115 (2020/10/02)
The palladium-catalysed sp3 C?H arylation of a selection of saturated amine scaffolds was investigated using substituted picolinamide directing groups. On the bornylamine scaffold, highly selective monoarylation takes place using unsubstituted picolinamide or 3-methylpicolinamide, whereas a double C?H arylation occurs with other substituents present, becoming a significant product with 3-trifluoromethylpicolinamide. DFT calculations were used to help rationalise the effect of directing groups on the C?H palladation steps which were found experimentally to be irreversible. The substituted picolinamide directing groups were also examined on acyclic amine scaffolds and in many cases increased yields and selectivity could be obtained using methylpicolinamides. For a selection of other amine scaffolds, the yield of C?H arylation could be improved significantly using 3-methylpicolinamide as the directing group and/or 3-methylpentan-3-ol as the solvent. (Figure presented.).
Nitrogen introduction of spirobifluorene to form α-, β-, γ-, and δ-aza-9,9′-spirobifluorenes: New bipolar system for efficient blue organic light-emitting diodes
Wu, Peng,Zhu, Jun,Zhang, Zhen,Dou, Dehai,Wang, Hedan,Wei, Bin,Wang, Zixing
, p. 185 - 191 (2018/04/17)
Four aza-9,9′-spirobifluorenes (aza-SBFs) with nitrogen atom at different positions of one fluorene moiety were synthesized to study the structure-properties relationships. α-Aza-SBF and β-aza-SBF possessed almost completely separated the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), while γ-aza-SBF and δ-aza-SBF showed overlapped HOMO and LUMO orbitals. The aza-SBFs showed excellent bipolar features and good thermal stabilities than those of SBFs. The maximum current efficiencies (CE) of α-, β-, γ-, and δ-aza-SBF-based OLEDs were 28.8, 24.9, 25.5, and 27.2 cd/A, respectively. Compared to the SBF, all of four aza-SBFs showed better devices performances. The CE and power efficiency (PE) of OLED based on α-aza-SBF was 28.8 cd/A and 22.6 lm/W, while the SBF-based OLED was only 12.3 cd/A and 8.2 lm/W. The maximum external quantum efficiency of α-aza-SBF-based OLED was 15.4%, which was 2.5 times than that of the SBF-based one (6.6%) due to introduction of nitrogen improving electron transporting. Novel materials based on these components and their potential applications in organic electronics were expected due to their excellent bipolar features.
2-Aminomethyl piperidines as novel urotensin-II receptor antagonists
Jin, Jian,Wang, Yonghui,Wang, Feng,Shi, Dongchuan,Erhard, Karl F.,Wu, Zining,Guida, Brian F.,Lawrence, Sarah K.,Behm, David J.,Disa, Jyoti,Vaidya, Kalindi S.,Evans, Christopher,McMillan, Lynette J.,Rivero, Ralph A.,Neeb, Michael J.,Douglas, Stephen A.
, p. 2860 - 2864 (2008/12/22)
A series of 2-aminomethyl piperidines has been discovered as novel urotensin-II receptor antagonists. The synthesis, initial structure-activity relationships, and optimization of the initial hit that resulted in the identification of potent, cross-species active, and functional urotensin-II receptor antagonists such as 1a and 11a are described.