4042-30-2Relevant academic research and scientific papers
A new combination of cyclohexylhydrazine and IBX for oxidative generation of cyclohexyl free radical and related synthesis of parvaquone
Patil, Pravin C.,Akamanchi, Krishnacharya G.
, p. 1883 - 1886 (2017)
The present paper demonstrates a single-step and straightforward synthesis of parvaquone through intermediacy of cyclohexyl radical generated from novel combination of cyclohexylhydrazine and o-iodoxybenzoic acid and subsequently trapped by 2-hydroxy-1,4-naphthoquinone. Formation of cyclohexyl free radical using this new combination was reaffirmed by cyclohexylation of readily available 2-amino-1,4-naphthoquinone.
Visible light-promoted Selectfluor-mediated quinone functionalization with unactivated Csp3-H components
Kulthe, Arun D.,Nadiveedhi, Maheshwara Reddy,Mainkar, Prathama S.,Akondi, Srirama Murthy
, p. 115 - 124 (2021/03/16)
A visible light-promoted metal-free cross-dehydrogenative-coupling (CDC) method for the alkylation of 1,4-naphthoquinones is reported using Selectfluor as a hydrogen atom transfer (HAT) agent. This protocol is suitable for a variety of 1,4-naphthoquinones and Csp3-H compounds and it facilitates the formation of pharmaceutically important quinone scaffolds under mild conditions. Using this methodology, the antimalarial drug, parvaquone, was synthesized in a single step.
Tridentate 3-Substituted Naphthoquinone Ruthenium Arene Complexes: Synthesis, Characterization, Aqueous Behavior, and Theoretical and Biological Studies
Geisler, Heiko,Westermayr, Julia,Cseh, Klaudia,Wenisch, Dominik,Fuchs, Valentin,Harringer, Sophia,Plutzar, Sarah,Gajic, Natalie,Hejl, Michaela,Jakupec, Michael A.,Marquetand, Philipp,Kandioller, Wolfgang
, p. 9805 - 9819 (2021/06/30)
A series of nine RuII arene complexes bearing tridentate naphthoquinone-based N,O,O-ligands was synthesized and characterized. Aqueous stability and their hydrolysis mechanism were investigated via UV/vis photometry, HPLC-MS, and density functional theory calculations. Substituents with a positive inductive effect improved their stability at physiological pH (7.4) intensely, whereas substituents such as halogens accelerated hydrolysis and formation of dimeric pyrazolate and hydroxido bridged dimers. The observed cytotoxic profile is unusual, as complexes exhibited much higher cytotoxicity in SW480 colon cancer cells than in the broadly chemo- (incl. platinum-) sensitive CH1/PA-1 teratocarcinoma cells. This activity pattern as well as reduced or slightly enhanced ROS generation and the lack of DNA interactions indicate a mode of action different from established or previously investigated classes of metallodrugs.
Visible-light-mediated photoredox minisci C-H alkylation with alkyl boronic acids using molecular oxygen as an oxidant
Dong, Jianyang,Yue, Fuyang,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
supporting information, p. 12652 - 12655 (2020/11/02)
Herein, we report a protocol for direct visible-light-mediated Minisci C-H alkylation reactions of heteroarenes with alkyl boronic acids using molecular oxygen as the sole oxidant. This mild protocol uses an inexpensive, green oxidant; permits efficient functionalization of various N-heteroarenes with a broad range of primary and secondary alkyl boronic acids; and is scalable to the gram level. We demonstrated the practicality and sustainability of the protocol by preparing or functionalizing several pharmaceuticals and natural products.
BI-OAc-Accelerated C3-H Alkylation of Quinoxalin-2(1 H)-ones under Visible-Light Irradiation
He, Xiang-Kui,Lu, Juan,Zhang, Ai-Jun,Zhang, Qing-Qing,Xu, Guo-Yong,Xuan, Jun
supporting information, p. 5984 - 5989 (2020/08/12)
An efficient, photoredox-catalyst-free radical alkylation of quinoxalin-2(1H)-ones has been described. This reaction utilizes 4-alkyl-1,4-dihydropyridines (R-DHPs) as alkyl radical precursors and acetoxybenziodoxole (BI-OAc) as an electron acceptor to und
Visible-light-mediated minisci C-H alkylation of heteroarenes with 4-alkyl-1,4-dihydropyridines using O2as an oxidant
Dong, Jianyang,Liu, Yuxiu,Song, Hongjian,Wang, Qingmin,Xu, Wentao,Yue, Fuyang
supporting information, p. 5599 - 5604 (2020/09/21)
Herein, we report a protocol for direct visible-light-mediated Minisci C-H alkylation reactions of N-heteroarenes with 4-alkyl-1,4-dihydropyridines at room temperature with molecular oxygen as an oxidant. The protocol permits efficient functionalization of various N-heteroarenes with a broad range of cyclic and acyclic primary, secondary, and tertiary alkyl groups and is scalable to the gram level. This mild protocol uses an inexpensive, green oxidant and is suitable for late-stage C-H alkylation of complex nitrogen-containing molecules. We demonstrated its utility by preparing or functionalizing several pharmaceuticals and natural products.
Bismuth-catalyzed methylation and alkylation of quinone derivatives with tert-butyl peroxybenzoate as an oxidant
Yang, Jian,Dong, Yu,He, Shuai,Shi, Zhi-Chuan,Wang, Yu,Wang, Ji-Yu
, (2019/11/26)
A bismuth-catalyzed methylation of quinones in the presence of tert-butyl peroxybenzoate (TBPB) was developed via a radical reaction mechanism. Particularly, TBPB was used not only as an efficient oxidant, but also as a green methyl source in such transformation. Moreover, this method could also be efficiently extended to the alkylation of quinones. This reaction tolerated a series of functional groups and prepared a series of derivatives of vitamin K3 and benzoquinone. Notably, antimalarial parvaquone was synthesized by the reaction.
A free radical alkylation of quinones with olefins
Liu, Shuai,Shen, Tong,Luo, Zaigang,Liu, Zhong-Quan
supporting information, p. 4027 - 4030 (2019/04/30)
We demonstrated herein an Fe(iii)-mediated radical alkylation of quinones. A wide range of bioactive molecules with quinone motifs can be rapidly synthesized by using readily available and inexpensive NaBH4/NaBD4 with alkenes at room temperature under open flask conditions.
Naphthoquinone Derivatives, Benzoquinone Derivatives, and Anthracenedione Derivatives, Their Use and Novel Method for Preparation
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Paragraph 0137; 0138; 0148; 0149, (2019/02/02)
The present invention relates to: a novel manufacturing method of quinone derivatives or anthracenedione derivatives by a copper-catalyzed cross-dehydrogenation coupling reaction of naphthoquinone, benzoquinone or anthracenedione compounds with various cycloalkanes; naphthoquinone derivatives, benzoquinone derivatives and anthracenedione derivatives; and uses thereof. According to the novel manufacturing method of the present invention, since the naphthoquinone derivatives, benzoquinone derivatives or anthracenedione derivatives can be prepared in one step, manufacturing efficiency is improved and cost and time can be saved, and the derivatives according to the present invention can be variously used as an animal medicine.COPYRIGHT KIPO 2019
Metal-, Photocatalyst-, and Light-Free, Late-Stage C-H Alkylation of Heteroarenes and 1,4-Quinones Using Carboxylic Acids
Sutherland, Daniel R.,Veguillas, Marcos,Oates, Conor L.,Lee, Ai-Lan
supporting information, p. 6863 - 6867 (2018/11/21)
Contrary to the accepted convention, this work shows that Minisci-type C-H alkylation does not require any metal, photocatalyst, light, or prefunctionalization of the readily available and inexpensive carboxylic acids to proceed well under mild conditions. These mild conditions can be utilized for late-stage alkylations of complex molecules, including pharmaceutical compounds and light-sensitive compounds which degrade under photocatalytic conditions.
