- Reactions of methyl esters of adamantane acids with acetonitrile
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Methyl adamantane-1-carboxylate and methyl (1-adamantyl)acetate react with acetonitrile in the presence of sodium hydride to give 3-(1-adamantyl)-3-oxopropanenitrile and 4-(1-adamantyl)-3-oxobutanenitrile, respectively. Reaction involving methyl (1-adamantyl)-acetate produces also 2-(1-adamantyl)-N-(E-1-cyanoprop-1-ene-2-yl)acetamide; the structure of this side product was established by X-ray diffraction analysis.
- Shiryaev,Belen′kaya,Shiryaev,Rybakov,Klimochkin, Yu. N.
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- Microwave-assisted synthesis of chiral nopinane-annelated pyridines by condensation of pinocarvone oxime with enamines promoted by FeCl3 and CuCl2
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Reaction of pinocarvone oxime with enamines and FeCl3 or CuCl2 resulted in annulation of nopinane carbon frame with pyridine and regioselective formation of chiral nopinane-annelated pyridines in 20-39% yields. Chemical structure of the pyridine derivatives were proved by precise NMR study.
- Vasilyev, Eugene S.,Agafontsev, Alexander M.,Tkachev, Alexey V.
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- Double-twist pyridine-carbonitrile derivatives yielding excellent thermally activated delayed fluorescence emitters for high-performance OLEDs
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Possessing high photoluminescence quantum yield (PLQY) and fast reverse intersystem crossing (RISC) process are critical for obtaining efficient thermally activated delayed fluorescence (TADF) emitters. Herein, two donor-spacer-acceptor molecules, namely, 4-(4-(9,9-dimethylacridin-10(9H)-yl)phenyl)-2,6-dimethylpyridine-3,5-dicarbonitrile (Me-DMAC) and 4-(4-(10H-phenoxazin-10-yl)phenyl)-2,6-dimethylpyridine-3,5-dicarbonitrile (Me-PXZ), were developed via a double-twist design strategy. The large hindrance induces a twisted geometry, leading to small ΔEST values and fast RISC processes. The time-resolved photophysical measurements revealed the TADF emissions of these pyridine-3,5-dicarbonitrile-based molecules in doped thin films. High external quantum efficiency (EQE) values of 25.8% and 21.1% were achieved in organic light-emitting diodes (OLEDs) using green Me-DMAC and yellow Me-PXZ dyes, respectively, as emitters.
- Li, Jiafang,Chen, Wen-Cheng,Liu, He,Chen, Zhanxiang,Chai, Danyang,Lee, Chun-Sing,Yang, Chuluo
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- Study of the Reactivity of the [(PE1CE2P)Ni(II)] (E1, E2 = O, S) Pincer System with Acetonitrile and Base: Formation of Cyanomethyl and Amidocrotononitrile Complexes versus Ligand Decomposition by P-S Bond Activation
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Nickel(II) chloride complexes with PE1CE2P (E = O, S) pincer ligands were used as precursors for the generation of cyanomethyl complexes in order to investigate the influence of variations (O vs S) in the side arms of the ligands on reactivity and stability of such compounds. In this regard, five hitherto unknown Ni(II) compounds were synthesized and fully characterized. Reaction of the Ni(II) chloride complex [(iPrPOCSPiPr)NiCl] (2-Cl) with 1 equiv of base and nitrile furnishes the cyanomethyl complex [(iPrPOCSPiPr)NiCH2CN] (2-CM). Increase of the amount of base and nitrile results in the formation of 3-amidocrotononitrile complexes [(iPrPOCOPiPr)NiNHC(CH3)CHCN] (1-ACN) and [(iPrPOCSPiPr)NiNHC(CH3)CHCN] (2-ACN). In contrast, similar reactions of the bis(thiophosphinite) complex 3-Cl resulted in formation of a tetranuclear Ni cluster (4) or a dinuclear 1,3-dithiolate-bridged PSCSP complex 5 by unexpected cleavage of P-S bonds of the pincer ligand.
- Hasche, Patrick,Spannenberg, Anke,Beweries, Torsten
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p. 4508 - 4515
(2019/11/14)
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- Acid-promoted rapid solvent-free access to substituted 1,4-dihydropyridines from β-ketothioamides
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β-Ketothioamides (KTAs) have been used as building blocks with aldehydes and β-enaminonitriles for synthesis of 1,4-dihydropyridines in the presence of AcOH under solvent-free conditions within 5 min. This new strategy exhibits remarkable features such as high chemoselectivity, mild reaction conditions, easily available substrates, and good yields.
- Li, Ming,Sun, Ke-Na,Wen, Li-Rong
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p. 21535 - 21539
(2016/03/08)
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- Direct β-acyloxylation of enamines via PhIO-mediated intermolecular oxidative C-O bond formation and its application to the synthesis of oxazoles
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A direct β-acyloxylation of enamine compounds has been achieved by using iodosobenzene (PhIO) as an oxidant to realize the intermolecular oxidative C(sp2)-O bond formation between enamines and various carboxylic acids, including N-protected amino acids. The transformation tolerates a wide range of functional groups and furnishes a variety of β-acyloxy enamines that can be conveniently converted to oxazole compounds via cyclodehydration.
- Liu, Xin,Cheng, Ran,Zhao, Feifei,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
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supporting information
p. 5480 - 5483,4
(2012/12/12)
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- Direct β-acyloxylation of enamines via PhIO-mediated intermolecular oxidative C-O bond formation and its application to the synthesis of oxazoles
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A direct β-acyloxylation of enamine compounds has been achieved by using iodosobenzene (PhIO) as an oxidant to realize the intermolecular oxidative C(sp2)-O bond formation between enamines and various carboxylic acids, including N-protected amino acids. The transformation tolerates a wide range of functional groups and furnishes a variety of β-acyloxy enamines that can be conveniently converted to oxazole compounds via cyclodehydration.
- Liu, Xin,Cheng, Ran,Zhao, Feifei,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
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supporting information
p. 5480 - 5483
(2013/01/15)
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- Highly efficient RhI-catalyzed asymmetric hydrogenation of β-amino acrylonitriles
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(Figure Presented) It takes two to TangPhos: β-Amino acrylonitriles can be readily prepared from acetonitriles. Both of the E/Z isomers undergo hydrogenation with excellent enantioselectivity by using the Rh-TangPhos (TangPhos = l, 1'-ditert-butyl-(2, 2')-diphospholane) catalyst system. The products, chiral β-amino nitriles, are valuable chiral building blocks for many drugs.
- Ma, Miaofeng,Hou, Guohua,Sun, Tian,Zhang, Xiaowei,Li, Wei,Wang, Junru,Zhang, Xumu
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supporting information; experimental part
p. 5301 - 5304
(2010/09/08)
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