Article
Chemistry, Multidisciplinary
Zhihui Shao, Xiaoyu Zhang, Xinyan Li, Weilin Wang, Jiaqiao Ding, Bing Cui, Mingqin Zhao
Summary: An efficient and green method for the synthesis of tetrahydro-beta-carbolines using a dehydrogenative coupling reaction between alcohols and tryptamines is reported. The reaction proceeds under mild conditions with the presence of a catalytic amount of (PNP)-P-iPr Mn catalyst and a weak base (Na2CO3). This strategy shows good tolerance towards various benzylic and aliphatic alcohol substrates with different functional groups, leading to diverse products in good to excellent yields.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Zhen Luo, Zheng-Qiang Liu, Ting-Ting Yang, Xin Zhuang, Chuan-Ming Hong, Fei-Fei Zou, Zhi-Yong Xue, Qing-Hua Li, Tang-Lin Liu
Summary: A highly selective and catalyst-free sulfonation of allylic alcohols with sulfinyl amides has been achieved, providing a convenient way to synthesize various allylic sulfones under mild conditions. This novel reaction exhibits broad substrate scope and excellent functional group tolerance, and can also be scaled-up. In addition, sulfinyl amides have been found to act as powerful sulfur nucleophiles in this reaction. Moreover, the solvent 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) plays a crucial role in allylic sulfonation.
Article
Chemistry, Organic
Zhang Xiaoyu, Li Xinyan, Cui Bing, Shao Zhihui, Zhao Mingqin
Summary: In this study, a new Pictet-Spengler oxidation reaction was developed using a pincer manganese catalyst, leading to the synthesis of 12 THBC products. The compounds exhibited good antioxidant activity, indicating their potential application in various fields.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Haiting Yin, Qin Ma, Yushan Wang, Xiaoxia Gu, Zhijun Feng, Yunjun Wu, Ming Wang, Shaoyin Wang
Summary: The study presents a facile and efficient route to tetrahydro-beta-carbolines from 2-indolylmethyl azides and propargylic alcohols via acid-catalyzed dehydrative annulation reactions. The reaction involves a cascade sequence of Friedel-Crafts-type alkylation followed by intramolecular Click reaction, forming multiple chemical bonds in a single operation with excellent atom-economy and broad functional group tolerance.
Article
Chemistry, Organic
Fan Xiao, Shi-Ming Xu, Xiu-Qin Dong, Chun-Jiang Wang
Summary: The Ir-catalyzed asymmetric tandem allylation/iso-Pictet-Spengler cyclization reaction provides a direct and practical approach for accessing tetrahydro-gamma-carboline derivatives with multiple functional groups and stereogenic centers in good to high yields and excellent stereoselective control. The wide substrate generality, easily available substrates, and simple chiral catalytic system demonstrate the great potential practicality of this efficient protocol.
Article
Biochemistry & Molecular Biology
Takuto Shimizu, Emiko Nogami, Yuka Ito, Kazuo Morikawa, Masaki Nagane, Tadashi Yamashita, Tsuyoshi Ogawa, Fuyuki Kametani, Hisashi Yagi, Naomi Hachiya
Summary: Prion disease is a neurodegenerative disorder with no effective therapeutic agents developed so far.
NEUROCHEMICAL RESEARCH
(2021)
Article
Chemistry, Multidisciplinary
Rina Mahato, Chinmoy Kumar Hazra
Summary: In this study, pentafluorophenol was revealed as an effective catalyst for the synthesis of (spirocyclic) tetrahydro-beta-carbolines via the Pictet-Spengler reaction. This straightforward catalytic system operates under mild conditions, yielding indole alkaloids in excellent yield and exhibiting remarkable functional group tolerance, including late-stage modifications. This transformation provides a practical and adaptable approach for the gram-scale synthesis of the natural alkaloid Komavine and enables the synthesis of the commercial drug Tadalafil.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Kadiyala Sagar, Tapas R. Pradhan, Abdikani Omar Farah, Henry R. Wise, Bhailal C. Merja, Malempati Srimannarayana, Paul Ha-Yeon Cheong, Jin Kyoon Park
Summary: The assistance of 1,1,1,3,3,3-hexafluoro-2-propanol enables the metal-free synthesis of 1,3-diamines via regioselective intermolecular interception of amines. N-chemoselectivity and regioselectivity are achieved for a wide range of substrates. Mechanistic studies and computational calculations provide insights into the reaction pathway and selectivity control.
Article
Chemistry, Organic
Arka Das, Christine Jonathan, Rana Saha, Md Imran Ahmed, Subhendu Bhowmik
Summary: A regioselective decarboxylative alkynylation of tetrahydro-beta-carboline-1-carboxylic acid under peroxide-free condition is reported, which exhibits high selectivity for the 1-position of tetrahydro-beta-carboline. Depending on the reagent, the reaction can produce alkynylated or enaminone products. The reaction proceeds through sequential decarboxylative iminium ion formation followed by an alkynylation and oxidative rearrangement cascade.
Article
Chemistry, Organic
Meng Wang, Ze-Hong Zheng, Mu-Qiu Chen, Gu Zhan, Jie Wang, Qian-Qian Yang, Wei Huang
Summary: A series of tetrahydro-beta-carbolin 1,3-diketone frameworks can be synthesized efficiently under mild conditions using azlactones and indole-2-amides. This reaction exhibits excellent compatibility and can be completed without a metal mediator.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Polymer Science
Semen Goreninskii, Nadezhda Danilenko, Evgeniy Bolbasov, Anastasia Evtina, Mikhail Buldakov, Nadezhda Cherdyntseva, Muhammad Saqib, Natalia Beshchasna, Joerg Opitz, Victor Filimonov, Sergei Tverdokhlebov
Summary: The PVP-containing PCL/PVP scaffolds fabricated using HFIP showed an enhanced strengthening effect and hydrophilicity, making them suitable for drug delivery systems.
JOURNAL OF APPLIED POLYMER SCIENCE
(2021)
Article
Chemistry, Organic
Jay Prakash Soni, Manda Sathish, Fabiane M. Nachtigall, Leonardo S. Santos, Nagula Shankaraiah
Summary: The Pictet-Spengler reaction is an efficient synthetic tool for constructing tetrahydro-beta-carbolines and tetrahydroisoquinolines, with a brown seaweed-derived alginic acid reported as an effective reusable catalyst. The protocol shows good yields with various aliphatic and aromatic aldehydes, and demonstrates sustainable synthesis of different compounds including a natural spirooxindole. The catalyst was found to be reusable with no significant deterioration in reaction yields observed up to the 6th cycle.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Gunjan, Pankaj Sharma, Pradeep Kumar, Nutan Sharma, Sunita Bhagat
Summary: Natural products are important in drug discovery and development, but their synthesis is a major challenge. This study reports an environmentally friendly synthesis of beta-carboline derivatives using the Pictet-Spengler reaction. Stellarines A and B, natural products with anti-inflammatory activity, were also synthesized from these derivatives. The synthetic strategy uses non-toxic and inexpensive materials, and the derivatives were evaluated for activity against SARS-CoV-2 Mpro(7BQY) using molecular docking studies.
Article
Chemistry, Physical
Bowei Wu, Nathan A. Seifert, Soenke Oswald, Wolfgang Jaeger, Yunjie Xu
Summary: The structures and binding topologies of two binary van der Waals complexes were investigated, revealing different binding configurations of rare gas atoms attached to HFIP. While multiple isomers were predicted for each complex, only the most stable one was detected experimentally. The effects of fluorination and comparison with other binary complexes were also discussed.
JOURNAL OF PHYSICAL CHEMISTRY A
(2021)
Article
Chemistry, Multidisciplinary
Yogesh Brijwashi Sharma, Rajveer Singh, Chetan Paul Singh, Yogesh P. Bharitkar, Abhijit Hazra
Summary: In this study, a one-step synthesis of tetrahydro-beta-carbolino-spiroindolone/spiroacenapthylene scaffold from tryptamine and isatin was achieved using lemon juice as a biocatalyst system via Pictet-Spengler Reaction. The reaction provided clean and convenient synthesis of spiroindolones. The product was separated and characterized using chromatographic and spectroscopic techniques. Bio evaluation showed promising activity against several cancer cell lines for specific compounds.
