605-88-9Relevant academic research and scientific papers
Rhodium-Catalyzed C-H Annulation of Free Anilines with Vinylene Carbonate as a Bifunctional Synthon
Nan, Jiang,Yin, Jiacheng,Gong, Xue,Hu, Yan,Ma, Yangmin
supporting information, p. 8910 - 8915 (2021/11/24)
Chemical transformation with vinylene carbonate as an emerging synthetic unit has recently attracted considerable attention. This report is a novel conversion pattern with vinylene carbonate, in which such a vibrant reagent unprecedentedly acts as a difunctional coupling partner to complete the C-H annulation of free anilines. From commercially available substrates, this protocol leads to the rapid construction of synthetically versatile 2-methylquinoline derivatives (43 examples) with excellent functionality tolerance.
Bifunctional thiophosphinamide catalyzed highly enantioselective Michael addition of acetone to (E)-2-azido β-nitrostyrenes and the subsequent reductive cyclization
Zhang, Hao,Wang, Youming,Zhou, Zhenghong
, p. 6071 - 6077 (2018/09/12)
We have proven that primary amine/thiophosphinamide incorporating (1R,2R)-1,2-diphenylethane-1,2-diamine is an efficient catalyst for the asymmetric Michael addition of acetone to (E)-2-azido β-nitrostyrenes. Under the optimal reaction conditions, the corresponding Michael addition products were obtained in excellent yields with almost perfect stereocontrol. Upon treatment with Et3SiH/InCl3, the Michael addition products could be successfully converted to the related 2-methyltetrahydroquinolines in acceptable yields with moderate to excellent diastereoselectivity and without appreciable loss in optical purity. This process provides a highly enantioselective pathway for the synthesis of biologically important 2-methyltetrahydroquinoline derivatives.
Synthesis of benzoquinoline derivatives from formyl naphthylamines via Friedl?nder annulation under metal-free conditions
Malinowski, Zbigniew,Fornal, Emilia,Warpas, Anna,Nowak, Monika
, p. 1999 - 2011 (2018/09/25)
Abstract: The synthesis of benzoquinolines and benzoquinolinones via Friedl?nder-type condensation of aminonaphthalene carbaldehydes with (1) primary or secondary alcohols mediated by urea/KOH or with (2) diketones or β-ketoesters is described. The behavi
Metallaphotoredox-Mediated Csp2-H Hydroxylation of Arenes under Aerobic Conditions
Shah, Sk. Sheriff,Paul, Amrita,Bera, Manoranjan,Venkatesh, Yarra,Singh, N. D. Pradeep
, p. 5533 - 5536 (2018/09/21)
The direct hydroxylation of 2-arylpyridines and 2-arylbenzothiazoles via the merger of organic photoredox and metal catalysis is reported where 4CzIPN is used as the visible-light photocatalyst and Pd(OAc)2 as the metal catalyst. This method has been employed to synthesize organic molecules exhibiting excited-state intramolecular proton transfer properties for generating tunable luminescence responses.
Traceless Directing-Group Strategy in the Ru-Catalyzed, Formal [3 + 3] Annulation of Anilines with Allyl Alcohols: A One-Pot, Domino Approach for the Synthesis of Quinolines
Kumar, Gangam Srikanth,Kumar, Pravin,Kapur, Manmohan
supporting information, p. 2494 - 2497 (2017/05/24)
A unique, ruthenium-catalyzed, [3 + 3] annulation of anilines with allyl alcohols in the synthesis of substituted quinolines is reported. The method employs a traceless directing group strategy in the proximal C-H bond activation and represents a one-pot Domino synthesis of quinolines from anilines.
Assembly of Diversely Substituted Quinolines via Aerobic Oxidative Aromatization from Simple Alcohols and Anilines
Li, Jixing,Zhang, Jinlong,Yang, Huameng,Jiang, Gaoxi
supporting information, p. 3284 - 3290 (2017/03/23)
An aerobic oxidative aromatization of simple aliphatic alcohols and anilines under the Pd(OAc)2/2,4,6-Collidine/Br?nsted acid catalytic system has been established, providing a direct approach for the preparation of diverse substituted quinoline derivatives in high yields with wide functional group tolerance. Practically, the protocol can be easily scaled up to gram-scale and was utilized in the concise formal synthesis of a promising herbicide candidate.
Transition-Metal-Free Regioselective Alkylation of Pyridine N-Oxides Using 1,1-Diborylalkanes as Alkylating Reagents
Jo, Woohyun,Kim, Junghoon,Choi, Seoyoung,Cho, Seung Hwan
supporting information, p. 9690 - 9694 (2016/08/10)
Reported herein is an unprecedented base-promoted deborylative alkylation of pyridine N-oxides using 1,1-diborylalkanes as alkyl sources. The reaction proceeds efficiently for a wide range of pyridine N-oxides and 1,1-diborylalkanes with excellent regioselectivity. The utility of the developed method is demonstrated by the sequential C?H arylation and methylation of pyridine N-oxides. The reaction also can be applied for the direct introduction of a methyl group to 9-O-methylquinine N-oxide, thus it can serve as a powerful method for late-stage functionalization.
Discovery and efficient synthesis of a biologically active alkaloid inspired by thiostrepton biosynthesis
Zheng, Qingfei,Wang, Shoufeng,Liu, Wen
, p. 7686 - 7690 (2014/12/10)
Thiostrepton, a natural peptide macrocycle, is of great interest due to its structural complexity and numerous biological activities, including anti-bacterial, anti-tumor, and anti-plasmodial activities. The quinaldic acid (QA) moiety-containing side ring (loop 2) was proven to play an important role in carrying out these functions. Previously, we proposed biosynthetic logic for thiostrepton loop 2 and demonstrated the formation mechanism of QA. Herein, we report the discovery and efficient synthesis of a biologically active alkaloid, that is, a key intermediate involved in the thiostrepton biosynthetic pathway. A chemo-enzymatic method was performed to synthesize the molecule, and a series of analogs were prepared for bioassays, which included the examination of anti-bacterial and anti-tumor activities.
A facile synthesis of substituted 2-alkylquinolines through [3 + 3] annulation between 3-ethoxycyclobutanones and aromatic amines at room temperature
Shan, Gang,Sun, Xiuyun,Xia, Qian,Rao, Yu
supporting information; experimental part, p. 5770 - 5773 (2012/01/06)
An efficient single-step approach toward the synthesis of 2-alkylquinolines is described. Through a Lewis acid mediated [3 + 3] annulation reaction between 3-ethoxycyclobutanones and aromatic amines, a variety of multisubstituted 2-alkylquinoline derivatives were prepared regioselectively at room temperature.
Assembly of substituted 2-alkylquinolines by a sequential palladium-catalyzed Ci-N and Ci-C bond formation
Matsubara, Yoshio,Hirakawa, Saori,Yamaguchi, Yoshihiro,Yoshida, Zen-Ichi
experimental part, p. 7670 - 7673 (2011/10/05)
Diversity: A range of substituted 2-alkylquinolines can be prepared in a general and efficient synthetic approach that employs mild reaction conditions (see scheme). The synthesis is based on a sequential palladium-catalyzed Ci-N and Ci-C bond formation, followed by palladium-catalyzed aromatization, and results in the formation of the desired compounds in one step. Copyright
