Article
Chemistry, Organic
Parul Pal, Meghan Fragis, Srinivas Dharavath, Jarrod W. Johnson, Jakob Magolan
Summary: Vinyl sulfides obtained by Wittig olefination with thioalkyl-phosphonium salts were used as aldehyde- or ketone surrogates in Fischer indole reactions. These vinyl sulfides reacted with arylhydrazines to yield diverse indole compounds. The utility of this chemistry was highlighted with the efficient preparation of three biomedically relevant compounds.
SYNTHESIS-STUTTGART
(2022)
Article
Biochemistry & Molecular Biology
Manohar D. Suryawanshi, Ganesh D. Suryawanshi, Pravin C. Mhaske, Dnyaneshwar G. Karpe, Komal R. Kamble, Sagar J. Rode, Vilas A. Sudrik, Shamrao P. Lawande
Summary: The Fischer indole synthesis reaction between phenylhydrazine and acetaldehyde produced 1H-indole, while the reaction of phenylhydrazine with malonaldehyde resulted in 1H-indole-3-carbaldehyde. Additionally, the Vilsmeier-Haack formylation of 1H-indole led to the formation of 1H-indole-3-carbaldehyde. Oxidation of 1H-indole-3-carbaldehyde produced 1H-indole-3-carboxylic acid. 1H-indole reacted with excess BuLi at -78 degrees C using dry ice also resulted in 1H-indole-3-carboxylic acid. The obtained 1H-indole-3-carboxylic acid was further converted to ester and acid hydrazide. Finally, the reaction between 1H-indole-3-carboxylic acid hydrazide and substituted carboxylic acid yielded indole-substituted oxadiazoles with antimicrobial activity. Synthesized compounds 9a-j showed promising in vitro antimicrobial activities against S. aureus bacteria compared to Streptomycin. Compound 9a, 9f, and 9g exhibited activities against E. coli compared to standards. Compound 9a and 9f demonstrated potent activity against B. subtilis compared to the reference standard, while compound 9a, 9c, and 9j were active against S. typhi.
CHEMISTRY & BIODIVERSITY
(2023)
Article
Chemistry, Multidisciplinary
Qingdong Hu, Chang Guo
Summary: The synthesis of structurally diverse multiligated platinum complexes, characterized by X-ray crystallography, opens up new reaction space and enables faster screening. The Pt/Cu dual catalytic system shows new cooperative reactivity, leading to the asymmetric synthesis of valuable functionalized indoles with good yields and excellent enantioselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Vania Graca, Ceu M. Sousa, Paulo J. Coelho
Summary: A simple synthesis method yielded molecules that quickly change color when exposed to UV or sunlight, with the ability to produce fast sunlight photoswitching materials at room temperature when incorporated into polymeric matrices.
Article
Biochemistry & Molecular Biology
Vasiliy M. Muzalevskiy, Zoia A. Sizova, Valentine G. Nenajdenko
Summary: In this study, a series of derivatives of 2-trifluoromethylindole were successfully synthesized through halogenation and base-catalyzed reactions, and the high synthetic utility of these compounds in reactions with various nucleophiles was demonstrated.
Article
Chemistry, Organic
Roman A. Irgashev, Alexander S. Steparuk, Gennady L. Rusinov
Summary: A series of compounds containing thieno[3,2-b]indole and coumarin parts were synthesized using a one-pot procedure. The synthesis was achieved by reacting 3-aminothieno[3,2-c]coumarins, generated in situ from 3-aminothieno[3,2-c]coumarin-2-carboxylates, with arylhyrazines. Additionally, the target compounds were successfully synthesized from available 4-hydroxycoumarins.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Zhenrong Liu, Zhiqiang Wang, Haiyan Liao, Zheng Li
Summary: An efficient method for constructing 1,2,3-triarylindoles through one-pot multicomponent reactions using calcium carbide, 3mol of iodoarenes, and aromatic amines as starting materials was described. This method allows for the simultaneous formation of five bonds in one step, resulting in a series of target products. The main advantages of this protocol include the use of a convenient alkyne source, a wide scope of substrates, and a simple workup procedure. The method can also be scaled up to gram scale.
Article
Chemistry, Organic
Yichen Qiu, Kararaina Te Puni, Clotilde C. Duplan, Ashley C. Lindsay, Jonathan Sperry
Summary: This study reports a method for obtaining tetrahydrocarbazoles through mechanochemical Fischer indolisation at ambient temperature.
TETRAHEDRON LETTERS
(2021)
Article
Multidisciplinary Sciences
Hilary M. Brown, Karan R. Doppalapudi, Patrick W. Fedick
Summary: Confined volume systems can accelerate chemical reactions, reduce waste, save time, and lower costs. This study demonstrates the application of acceleration techniques in improving synthetic routes, discovering novel reactions, and screening cage structure intermediates through exploration of different confined volume systems.
SCIENTIFIC REPORTS
(2021)
Review
Chemistry, Multidisciplinary
Nengzhong Wang, Zugen Wu, Junjie Wang, Nisar Ullah, Yixin Lu
Summary: The past two decades have seen remarkable growth of asymmetric organocatalysis, serving as a powerful platform for producing chiral molecules. Ring structures are widely present in organic compounds, and strategic construction of ring motifs is crucial in natural product synthesis.
CHEMICAL SOCIETY REVIEWS
(2021)
Article
Biochemistry & Molecular Biology
Asma Hrizi, Manon Cailler, Moufida Romdhani-Younes, Yvan Carcenac, Jerome Thibonnet
Summary: This study describes a method for the preparation of polysubstituted indole-2-carbonitriles through a cross-coupling reaction. The reactivity of indole derivatives with iodine at position 3 was studied using various cross-coupling reactions. Sonogashira, Suzuki-Miyaura, Stille, and Heck cross-couplings provided a variety of di-, tri- and tetra-substituted indole-2-carbonitriles.
Article
Chemistry, Organic
Katia Martina, Giancarlo Cravotto, Rajender S. Varma
Summary: Microwave-assisted organic synthesis has become a mature technology with numerous advantages in terms of reaction rate and yield, and it also helps in scaling up production.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Organic
Tohasib Yusub Chaudhari, Vibha Tandon
Summary: This review summarizes synthetic methodologies for tetrahydrocarbazole (THC) published in the last ten years, focusing on non-enantioselective syntheses such as ring opening reactions of donor-acceptor cyclopropanes, metal-catalyzed bond formation, cycloaddition, conjugate addition, and other reactions used for accessing the THC framework.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Xin-Wei Wang, Xiang Li, Mu-Wang Chen, Bo Wu, Yong-Gui Zhou
Summary: Chiral phosphoric acid-catalyzed Pictet-Spengler reactions have been successfully employed to synthesize a series of novel compounds with excellent yields and high enantiomeric excess.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Xin-Peng Mu, Yuan-He Li, Nan Zheng, Jian-Yu Long, Si-Jia Chen, Bing-Yan Liu, Chun-Bo Zhao, Zhen Yang
Summary: A novel method for the synthesis of cyclohepta[b]indoles in high yields was developed through a visible-light-induced, photocatalyzed [2+2]-cycloaddition/ retro-Mannich-type reaction of enaminones. Experimental and computational studies indicated that the reaction is initiated by single-electron oxidation of an enaminone moiety, leading to cyclobutane formation and rapid fragmentation in a radical-cation state to produce cyclohepta[b]indoles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Ryan M. Bain, Christopher J. Pulliam, Shannon A. Raab, Graham Cooks
JOURNAL OF CHEMICAL EDUCATION
(2016)
Article
Chemistry, Multidisciplinary
Ryan M. Bain, Christopher J. Pulliam, Shannon A. Raab, R. Graham Cooks
JOURNAL OF CHEMICAL EDUCATION
(2015)
Article
Chemistry, Multidisciplinary
Ryan M. Bain, Christopher J. Pulliam, R. Graham Cooks
Article
Chemistry, Analytical
Ryan M. Bain, Xin Yan, Shannon A. Raab, Stephen T. Ayrton, Tawnya G. Flick, R. Graham Cooks
Review
Chemistry, Multidisciplinary
Xin Yan, Ryan M. Bain, R. Graham Cooks
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2016)
Article
Chemistry, Multidisciplinary
Ryan M. Bain, Christopher J. Pulliam, Fabien Thery, R. Graham Cooks
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2016)
Article
Chemistry, Applied
Xin Yan, Ryan M. Bain, Yafeng Li, Ran Qiu, Tawnya G. Flick, R. Graham Cook
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2016)
Article
Biochemical Research Methods
Ryan M. Bain, Christopher J. Pulliam, Stephen T. Ayrton, Kinsey Bain, R. Graham Cooks
RAPID COMMUNICATIONS IN MASS SPECTROMETRY
(2016)
Article
Physics, Atomic, Molecular & Chemical
Patrick W. Fedick, Ryan M. Bain, Shunshun Miao, Valentina Pirro, R. Graham Cooks
INTERNATIONAL JOURNAL OF MASS SPECTROMETRY
(2017)
Article
Biochemical Research Methods
Yin-Hung Lai, Shyam Sathyamoorthi, Ryan M. Bain, Richard N. Zare
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY
(2018)
Article
Biochemical Research Methods
S. T. Ayrton, X. Chen, R. M. Bain, C. J. Pulliam, M. Achmatowicz, T. G. Flick, D. Ren, R. G. Cooks
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY
(2018)
Article
Biochemical Research Methods
John R. Stutzman, Ryan M. Bain, Sebastian Hagenhoff, William H. Woodward, John P. O'Brien, Michael Lesniak
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY
(2019)
Article
Oncology
Kanchustambham Vijayalakshmi, Vishnu Shankar, Ryan M. Bain, Rosalie Nolley, Geoffrey A. Sonn, Chia-Sui Kao, Hongjuan Zhao, Robert Tibshirani, Richard N. Zare, James D. Brooks
INTERNATIONAL JOURNAL OF CANCER
(2020)
Article
Chemistry, Multidisciplinary
Ryan M. Bain, Shyam Sathyamoorthi, Richard N. Zare
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)