- Pd-Catalyzed Carbonylative Synthesis of 4H-Benzo[d][1,3]Oxazin-4-Ones Using Benzene-1,3,5-Triyl Triformate as the CO Source
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A facile synthesis of 4H-benzo[d][1,3]oxazin-4-one derivatives by Pd-catalyzed carbonylative cross-coupling between N-(ortho-bromoaryl)amides and benzene-1,3,5-triyl triformate (TFBen) was developed. This procedure does not require the toxic and flammable gas CO as the carbonyl source and tolerates a wide scope of functional groups. Remarkably, 4H-benzo[d][1,3]oxazin-4-ones incorporated to natural products and drugs can be constructed by this method.
- Zheng, Yan,Dong, Mengke,Qu, Erdong,Bai, Jin,Wu, Xiao-Feng,Li, Wanfang
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supporting information
p. 16219 - 16224
(2021/10/06)
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- Rhodium-Catalyzed ortho-Bromination of O-Phenyl Carbamates Accelerated by a Secondary Amide-Pendant Cyclopentadienyl Ligand
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It has been established that a newly developed cyclopentadienyl rhodium(III) [CpARhIII] complex, bearing an acidic secondary amide moiety on the Cp ring, is able to catalyze the ortho-bromination of O-phenyl carbamates with N-bromosuccinimide (NBS) at room temperature. The presence of the acidic secondary amide moiety on the CpA ligand accelerates the bromination by the hydrogen bond between the acidic NH group of the CpA ligand and the carbonyl group of NBS.
- Tanaka, Jin,Shibata, Yu,Joseph, Anton,Nogami, Juntaro,Terasawa, Jyunichi,Yoshimura, Ryo,Tanaka, Ken
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supporting information
p. 5774 - 5779
(2020/05/08)
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- NOVEL PYRROLIDINYL AMIDE COMPOUNDS FOR THE TREATMENT OF AUTOIMMUNE DISEASE
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The present invention relates to compounds of formula (I) wherein R1, R2, R3 and R4 are as described herein, and their pharmaceutically acceptable salt, enantiomer or diastereomer thereof, and compositions inclu
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Page/Page column 17
(2020/03/23)
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- Site-Specific Synthesis of Carbazole Derivatives through Aryl Homocoupling and Amination
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We synthesized various carbazoles from anilines through a three-step process with good overall yields (up to 48percent). This process comprises N -acetylation, copper(0)-mediated Ullmann homocoupling, and acid-mediated intramolecular amination. It permits various functional groups on the substrate. Scale-up of the developed three-step synthetic route to carbazoles was also demonstrated.
- Baek, Junghyun,Ban, Jaeyoung,Lim, Minkyung,Rhee, Hakjune,Shabbir, Saira
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p. 917 - 927
(2020/03/13)
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- Iridium-catalyzed intramolecular C–N and C–O/S cross-coupling reactions: Preparation of benzoazole derivatives
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The irdium-catalyzed intramolecular arylcarbon-hetero cross-coupling reactions with o-haloarylamides or o-haloarylamidine have been effectively achieved using KOAc and just 1 mol% catalyst. The [Ir(cod)Cl]2 was proved to be more potential for smoothly assembling functional structures benzimidazoles, benzoxazoles and benzothiazoles, which was superior to Cu- and Pd-catalyzed systems. Simultaneously, a concise and efficient synthesis of tafamidis was developed in 5-g scale.
- Shi, Yajie,Zhou, Qifan,Du, Fangyu,Fu, Yang,Du, Yang,Fang, Ting,Chen, Guoliang
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supporting information
(2019/09/10)
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- Monoprotected l-Amino Acid (l-MPAA), Accelerated Bromination, Chlorination, and Iodination of C(sp2)?H Bonds by Iridium(III) Catalysis
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Halogenated arenes are important structural motifs commonly found in biologically active molecules and used for a variety of transformations in organic synthesis. Herein, we report the mono-protected l-amino acid (l-MPAA) accelerated iridium(III)-catalyzed halogenation of (hetero)anilides at room temperature. This reaction constitutes the first example of an iridium(III)/l-MPAA-catalyzed general halogenation of (hetero)arenes through C(sp2)?H activation. Furthermore, we demonstrate the potential utility of our method through its use in the synthesis of a quinolone derivative.
- Kathiravan, Subban,Nicholls, Ian A.
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p. 7031 - 7036
(2017/05/29)
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- POLYCYCLIC TLR7/8 ANTAGONISTS AND USE THEREOF IN THE TREATMENT OF IMMUNE DISORDERS
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The present invention relates to compounds of Formula (I) and pharmaceutically acceptable compositions thereof, useful as toll-like receptor 7/8 (TLR7/8) antagonists. In Formula (I), Ring A is aryl or heteroaryl; Ring B is aryl or heteroary; and X is C(R4)2, O, NR4, S, S(R4), or S(R4)2.
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Paragraph 00504
(2017/07/06)
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- A palladium-catalyzed regiospecific synthesis of N-aryl benzimidazoles
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(Chemical Equation Presented) Highly tolerated: A catalytic method employing [Pd2(dba)3] and XPhos or RuPhos permits the efficient synthesis of N-aryl benzimidazoles in regioisomerically pure form starting from ortho-halo-anilides (see scheme), and tolerates a wide range of functional groups, dba = trans,trans-dibenzylideneacetone.
- Zheng, Nan,Anderson, Kevin W.,Huang, Xiaohua,Nguyen, Hanh Nho,Buchwald, Stephen L.
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p. 7509 - 7512
(2008/09/17)
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- Copper-catalyzed regiospecific synthesis of N-alkylbenzimidazoles
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(Chemical Equation Presented) A copper-catalyzed method is described for the preparation of N-alkylbenzimidazoles in regioisomerically pure form starting from o-haloanilines. The method utilizing CuI and trans-N,N′-dimethyl-1, 2-cyclohexanediamine allows the preparation of N-alkylbenzimidazoles in good to excellent yields.
- Zheng, Nan,Buchwald, Stephen L.
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p. 4749 - 4751
(2008/03/14)
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- ONE-POT REDUCTIVE ACETAMIDATION OF ARYL NITRO COMPOUNDS
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The present invention provides a method for the reductive acetamidation of an aryl nitro compound by reacting a substituted acid with an aryl nitro compound and adding a catalytic amount of a base with the substituted acid and the aryl nitro compound to form an acetamidation aryl nitro compound. The acetamidation aryl nitro compound is then purified.
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Page/Page column 10
(2008/06/13)
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- Novel substituted tricyclic compounds
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Compounds of the general formula (I) are useful in the treatment and prevention of β3-related diseases including diabetes, obesity and hyperlipidemia wherein R1 is hydrogen, halogen, or hydroxyl; R2 is C1-4 alkyl or benzyl
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