Article
Chemistry, Organic
Si-Si Ning, Dan Meng, Jie-Yun Zhang, Shi-Lei Liu, Ni-Ni Zhou, Xiaojie Jin, Hai-Tao Zhu
Summary: A metal-free intramolecular [3+2] cycloaddtion of benzene-linked propynol-ynes in AcOH/H2O has provided a greener and more practical route to functionalized naphtho[1,2-c]furan-5-ones with high regioselectivity. Additionally, regioselective alpha-deuteration of the naphtho[1,2-c]furan-5-ones showed excellent deuterium incorporation and yields. The fluorescent properties of the naphtho[1,2-c]furan-5-one products were also investigated in solution.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Xiangrong Liu, Xue Tian, Jiawu Huang, Yu Qian, Xinfang Xu, Zhenghui Kang, Wenhao Hu
Summary: An enantioselective three-component reaction of alpha-propargylic-3-indolymethanol with diazoindolinone and alcohol has been achieved under the cocatalysis of Rh(II) and chiral phosphoric acid (CPA). The reaction proceeds through regio- and enantiospecific addition of an in situ formed oxonium ylide to the alpha-propargylic indole iminium ion, providing an efficient access to chiral propargylic indole derivatives with high yields and enantioselectivities.
Article
Chemistry, Organic
Juan J. Rojas, Elena Torrisi, Maryne A. J. Dubois, Riashat Hossain, Andrew J. P. White, Giovanni Zappia, James J. Mousseau, Chulho Choi, James A. Bull
Summary: This paper reports a method for synthesizing 1,4-dioxanes and explores the catalytic mechanism of the reaction. The reaction exhibits high regio- and diastereoselectivity, and the resulting products serve as interesting motifs for drug discovery.
Article
Chemistry, Organic
Yingying Zhang, Yating Huang, Kewei Yu, Xiaoxiang Zhang, Wenhua Yu, Jiale Tang, Yiran Tian, Wanxing Wei, Zhuan Zhang, Taoyuan Liang
Summary: Herein, we report a novel iron and iodine cooperative catalytic system for the synthesis of diverse 2-amino-3-alkylindoles. The method exhibits good substrate and functional group compatibility, and the catalyst system and feedstocks are readily available, showing great potential for further exploration of biological activities.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Qiwen Gao, Jinhong Tian, Kangmei Wen, Chen Chen, Xingang Yao, Jianxin Pang, Xiaodong Tang
Summary: In this study, a copper-mediated C4-benzylation reaction of 5-aminopyrazoles with 3-indoleacetic acids was presented. Various benzylated 5-aminopyrazoles were synthesized in good-to-excellent yields under basic and ligand-free conditions in the presence of copper acetate. The benzylation method was also applied to other substrates and showed potential antiproliferative activities against cancer cell lines. Moreover, the C4-benzylated products underwent cyclization with aldehydes to form 1H-pyrazolo-[4 ',3 ':6,7]-azepino-[3,4-b]-indoles via one-pot two-step processes. The cyclized products exhibited fluorescence emissions with large Stokes shifts.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Braja Gopal Das, Sadhna Shah, Arko Das, Vinod K. Singh
Summary: The first stereoselective propargylic dearomatization of 2-naphthol derivatives was achieved using a chiral Cu-II-L10 complex, leading to the formation of products with a contiguous all-carbon quaternary-tertiary stereocenter and a terminal alkyne functionality. Both reactions demonstrated excellent chemodivergent reactivity and yielded the desired products with high chemo- and stereoselectivities.
Article
Chemistry, Multidisciplinary
Ruo-Qing Wang, Chong Shen, Xiang Cheng, Xiu-Qin Dong, Chun-Jiang Wang
Summary: In this study, copper-catalyzed asymmetric propargylic substitution was successfully achieved using salicylaldehyde-derived imine esters and propargylic carbonates, resulting in a wide range of chiral amino acid derivatives containing propargylic groups. The ortho-hydroxy group of the salicylaldehyde-derived imine esters played a crucial role in increasing reactivity and stabilizing the azomethine ylide.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Yucheng Wang, Bo Wang, Zhihui Ren, Zheng-Hui Guan
Summary: An efficient method using copper catalysis was developed to access beta-alkynyl ketones from propargylic alcohols and enamides. This methodology provides a series of highly functionalized beta-alkynyl ketones in moderate to excellent yields under mild conditions. Furthermore, the resulting products can be transformed into valuable scaffolds with potential biological activities.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Aleksey Zerov, Irina A. Boyarskaya, Olesya Khoroshilova, Irina N. Lavrentieva, Alexander Slita, Ekaterina O. Sinegubova, Vladimir V. Zarubaev, Aleksander V. Vasilyev
Summary: Trimethylsilyl ethers of 1,5-diaryl-3-(trifluoromethyl)pent-1-en-4-yn-3-oles in the superacid TfOH give rise to reactive conjugated CF3-allylic-propargylic cations, which, in the presence of arenes and excess TfOH, lead to the formation of E-1,1,5-triaryl-3-(trifluoromethyl)-pent-2-en-4-ynes and CF3-bicyclic dihydroanthracene derivatives, respectively. These two main reaction pathways are dependent on the nucleophilicity of aryl substituents in CF3-pentenynes and external aromatic molecules.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Bhaskar B. Dhotare, Sahil Kumar, Amey Wadawale, Sandip K. Nayak, Mukesh Kumar, Dibakar Goswami
Summary: A novel metal-free approach for the synthesis of various 3-substituted-3-arylbenzofuran-2(3H)-ones has been developed via H2SO4-mediated dehydrative substitution, yielding moderate to good yields. Mechanistically, the substitution with the alkoxy group proceeds through a phenolic-hydroxyester intermediate, forming the desired product through cascade dehydration-relactonization steps.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Tatsuhiro Uchikura, Irene Sanchez-Sordo, Tatsuhiko Yoshimura, Yudai Makino, Hiroto Osakabe, Takahiko Akiyama
Summary: We have developed a chiral phosphoric acid-catalyzed enantioselective Friedel-Crafts alkylation reaction between pyrroles and indolylmethanols. Wide substrate scope was observed, and a chiral all-carbon quaternary center was constructed at the 3 position of indoles in high yields with high to excellent enantioselectivities (up to 99% ee).
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Karolina Dzedulionyte, Melita Veiksaite, Vit Moravek, Vida Malinauskiene, Greta Rackauskiene, Algirdas Sackus, Asta Zukauskaite, Egle Arbaciauskiene
Summary: A general approach for the synthesis of tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepin-4-one derivatives was developed. This approach involved a regioselective strategy for synthesizing ethyl 1-(oxiran-2-ylmethyl)-1H-pyrazole-5-carboxylates followed by ring-opening and cyclisation reactions to yield the target compounds. A straightforward two-step method was also applied to functionalize other derivatives. The structures of the fused heterocyclic compounds were confirmed using spectroscopy techniques.
Article
Multidisciplinary Sciences
Jiayin Zhang, Xihao Chang, Xianghong Xu, Hongyi Wang, Lingzi Peng, Chang Guo
Summary: This study demonstrates the nickel-catalyzed dienylation and enantioselective allenylation of phosphine oxides, showing high selectivity in terms of chemo-, regio-, and enantioselectivity.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Dhananjay S. Nipate, Vikki N. Shinde, Krishnan Rangan, Anil Kumar
Summary: A condition-based switchable regioselective hydroalkylation of 2-arylindoles with maleimides has been developed. The reaction in the presence of a Ru(ii)-catalyst resulted in hydroalkylation at the ortho-position of the C2-aryl ring via C-H activation whereas the reaction in the absence of the catalyst in TFE resulted in C3-hydroalkylation. Various functional groups both on the indole ring and on the 2-phenyl ring were tolerated and a wide range of hydroalkylated products were obtained in moderate to high (37-88%) yields.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Mark G. Saulnier, Steven M. Schreiber, Kerri L. Cavanaugh, Robert B. Perni, H. Howard Joyner, Gordon W. Gribble
Summary: New examples of the 1,4-dihydropyrrolo[3,4-b]indol-3(2H)-one ring system were synthesized via Fischer indolization with high yields. The method involves lithiation at the C-1 position followed by quenching with iodomethane.
