- Synthesis of novel multifunctional pyridine-2,6-dicarboxylic acid derivatives
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Eleven novel multifunctional compounds with pyridine-2,6-dicarboxylic acid were synthesized by hydrolyzing of ester prepared by coupling of diethyl 4-hydroxypyridine-2,6-dicarboxylate to bis-halohydrocarbon or bis-halide. All of the new compounds were characterized by 1H NMR, MS, IR and EA.
- Yin, Xian-Hong,Tan, Min-Yu
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- Simple and Clean Photo-induced Methylation of Heteroarenes with MeOH
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Heteroarene methylation utilizing a cheap and safe methylation source without involving transition metals represents an important yet challenging objective. Here, a simple and clean catalyst-free protocol for the methylation of various heteroarenes (including six- and five-membered types) is described under light irradiation. This protocol employs cheap, readily available, and abundant MeOH as both the solvent and the methylation source. It was found that adding dichloromethane (DCM) as a co-solvent could significantly increase the yield of the methylation products. Heteroarenes bearing various functional groups could be methylated and tri-deuteromethylated successfully. Deuterium labeling studies suggested that the newly generated methyl group in the products consisted of two hydrogens from the methyl group and one hydrogen from the OH group in MeOH.
- Liu, Wenbo,Yang, Xiaobo,Zhou, Zhong-Zhen,Li, Chao-Jun
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supporting information
p. 688 - 702
(2017/05/15)
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- Alcohols as alkylating agents in heteroarene C-H functionalization
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Redox processes and radical intermediates are found in many biochemical processes, including deoxyribonucleotide synthesis and oxidative DNA damage. One of the core principles underlying DNA biosynthesis is the radical-mediated elimination of H2O to deoxygenate ribonucleotides, an example of 'spin-centre shift', during which an alcohol C-O bond is cleaved, resulting in a carbon-centred radical intermediate. Although spin-centre shift is a well-understood biochemical process, it is underused by the synthetic organic chemistry community. We wondered whether it would be possible to take advantage of this naturally occurring process to accomplish mild, non-traditional alkylation reactions using alcohols as radical precursors. Because conventional radical-based alkylation methods require the use of stoichiometric oxidants, increased temperatures or peroxides, a mild protocol using simple and abundant alkylating agents would have considerable use in the synthesis of diversely functionalized pharmacophores. Here we describe the development of a dual catalytic alkylation of heteroarenes, using alcohols as mild alkylating reagents. This method represents the first, to our knowledge, broadly applicable use of unactivated alcohols as latent alkylating reagents, achieved via the successful merger of photoredox and hydrogen atom transfer catalysis. The value of this multi-catalytic protocol has been demonstrated through the late-stage functionalization of the medicinal agents, fasudil and milrinone.
- Jin, Jian,MacMillan, David W. C.
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- Rh-catalyzed sequential oxidative C-H activation/annulation with geminal-substituted vinyl acetates to access isoquinolines
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The concise synthesis of 3-substituted or non-C3-substituted isoquinolines through Rh-catalyzed sequential oxidative C-H activation/annulation with geminal-substituted vinyl acetates was developed with good functional group tolerance. The protocol was successfully applied to the total synthesis of the natural product papaverine.
- Chu, Haoke,Sun, Song,Yu, Jin-Tao,Cheng, Jiang
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supporting information
p. 13327 - 13329
(2015/08/24)
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- SUBSTITUTED AROMATIC CARBOXAMIDE AND UREA DERIVATIVES AS VANILLOID RECEPTOR LIGANDS
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The invention relates to substituted aromatic carboxamide and urea derivatives, to processes for the preparation thereof, to pharmaceutical compositions containing these compounds and also to the use of these compounds for preparing pharmaceutical compositions (formula (I)).
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Page/Page column 142; 143
(2010/11/18)
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- AgOTf and TfOH co-catalyzed isoquinoline synthesis via redox reactions of O-alkyl oximes
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Under AgOTf and Br?nsted acid co-catalysis, O-alkyl o-alkynylbenzaldoxime derivatives undergo a cyclization-induced N-O cleavage to produce isoquinolines with the simultaneous oxidation of O-alkyl group. This redox-based method provides a general access t
- Hwang, Soojin,Lee, Youngun,Lee, Phil Ho,Shin, Seunghoon
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scheme or table
p. 2305 - 2308
(2009/09/06)
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- Synthesis of pyridine and isoquinoline derivatives by the palladium-catalyzed cyclization of olefinic ketone O-pentafluorobenzoyloximes
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Pyridines and isoquinolines are synthesized from olefinic ketone O-pentafluorobenzoyloximes by treatment with a catalytic amount of Pd(PPh3)4 in the presence of (n-Bu)4NCl and triethylamine.
- Tsutsui, Hironori,Narasaka, Koichi
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p. 526 - 527
(2007/10/03)
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- New Heteroaromatic Complexing Agents and Luminescence of Their Europium(III) and Terbium(III) Chelates
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Twelve heteroaromatic complexing agents 9a-l were synthesized with the purpose to develop suitable labels for time-resolved luminescence-based bioaffinity assays.The relative luminescence yields, excitation maxima, and emission decay constants of their europium(III) and terbium(III) chelates were determined.According to these results, 2,2',2'',2'''-tetrakis(acetic acid) (9e) and 2,2',2'',2'''-tetrakis(acetic acid) (9l) are the most promising agents.
- Mukkala, Veli-Matti,Sund, Christian,Kwiatkowski, Marek,Pasanen, Paavo,Hoegberg, Marita,et al.
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p. 1621 - 1632
(2007/10/02)
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- THERMOLYTIC RING OPENING OF ACYLOXYBENZOCYCLOBUTENES: AN EFFICIENT ROUTE TO 3-SUBSTITUTED ISOQUINOLINES
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Upon flash vacuum pyrolysis acyloxybenzocyclobutenes 4 rearrange through an intramolecular 1,5-acyl shift to 2-formylbenzyl ketones 6 which can be converted to 3-substituted isoquinolines 7.
- Schiess, Peter,Huys-Francotte, Martine,Vogel, Caspar
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p. 3959 - 3962
(2007/10/02)
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- A CONVENIENT SYNTHETIC METHOD OF 1,3-DISUBSTITUTED ISOQUINOLINES USING SILVER TRIFLUOROMETHANESULFONATE AS A KEY REAGENT
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1,3-Disubstituted isoquinolines were prepared under mild conditions from allylbenzenes and nitriles using silver trifluoromethanesulfonate and iodine.
- Sato, Tadashi,Tamura, Kunio,Nagayoshi, Kazuo
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p. 791 - 794
(2007/10/02)
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- REACTION OF BENZYL KETONES WITH NITRILES IN PRESENCE OF POCl3
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The reaction of benzyl ketones with nitriles in presence of POCl3 has been examined.It has been found that intermediate N-styrylimidoyl dichlorophosphates formed under reaction conditions undergo further reactions to isoquinoline and pyrimidine derivatives and form the products of fragmentation and condensation.The effect of structure of the substrates on the relative ratios of the products formed has been discussed.
- Zielinski, Wojciech
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- A NEW PHOTOCHEMICAL SYNTHETIC ROUTE TO 2,3-BENZODIAZEPINES FROM ISOQUINOLINE N-IMIDES
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Photolysis of the isoquinoline N-imides (6) under a basic condition gave the corresponding 5H-2,3-benzodiazepines (7), which were converted to the 3-acetyl-3H-2,3-benzodiazepines (11) by treatment with acetic anhydride.
- Enkaku, Michiko,Kurita, Jyoji,Tsuchiya, Takashi
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p. 1923 - 1926
(2007/10/02)
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