Article
Chemistry, Multidisciplinary
Nico Fleck, Rohan M. Thomas, Marcel Muller, Stefan Grimme, Bruce H. Lipshutz
Summary: This study presents an environmentally responsible synthesis of tezacaftor using chemistry in water enabled by a nonionic surfactant. The method reduces the overall E Factor by 54% compared to the existing route and demonstrates the role of micellar nanoreactors in the reaction.
Article
Chemistry, Organic
Mikiko Koshiba, Yuto Furuki, Kazuhiro Morisaki, Ryohei Doi, Yoshihiro Sato
Summary: We report a nickel-catalyzed migratory cycloisomerization reaction for the synthesis of 2,3-disubstituted indoles. The reaction proceeds via acyl transfer on the nitrogen atom of the substrate to the C3 position in the product, and a suitable N-heterocyclic carbene ligand is used in the reaction.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Hao Wu, Yi-Chun Wang, Andrey Shatskiy, Qiu-Yan Li, Jian-Quan Liu, Markus D. Karkas, Xiang-Shan Wang
Summary: A method using silver-catalyzed aerobic oxidation/6-endo heterocyclization of ortho-alkynylbenzaldehydes to produce 3-substituted isocoumarins has been developed. The protocol allows convenient access to a variety of useful compounds in good to high yields. Mechanistic studies suggest a free-radical pathway is involved.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Weiqiang Sun, Xueli Cui, Jing Qu, Xiaojia Cai, Jinhui Hu, Zhuang Xiong, Suqin Guo, Jun Xu, Wen-Hua Chen, Jia-Qiang Wu
Summary: This paper presents a practical and versatile oxidative cyclization reaction of 2-arylethynylanilines to form 2-hydroxy-2-substituted indol-3-ones using a copper-catalyzed radical approach in the presence of O-2. The transformation of 2-hydroxy-2-arylindol-3-ones to 3-hydroxy-3-arylindol-2-ones is efficient and demonstrates the practicality and utility of this catalytic system. Mechanistic investigations revealed that the acetyl substituent on 2-arylaethynylanilines plays a crucial role in the formation of the cyclic products through an N-center radical-based 5-endo-dig aza-cyclization pathway.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Chada Raji Reddy, Ketan Wadekar, Karna Nair, Y. Lakshmi Prapurna
Summary: A new approach for synthesizing benzofurans from non-aromatic precursors is reported. The method involves sequential DBU-mediated cycloisomerization for furanylation followed by benzene ring construction via oxidative aromatization. The reaction has advantages such as atom- and pot-economy, simple reaction conditions, easy preparation of starting materials, and access to diverse substituted benzofurans.
SYNTHESIS-STUTTGART
(2022)
Article
Biochemistry & Molecular Biology
Spyridon Dimitrakis, Efthymios-Spyridon Gavriil, Athanasios Pousias, Nikolaos Lougiakis, Panagiotis Marakos, Nicole Pouli, Katerina Gioti, Roxane Tenta
Summary: In this study, a series of pyrrolo[2,3-c]pyridines, pyrrolo[3,2-d]pyrimidines, and pyrazolo[4,3-d]pyrimidines were designed and synthesized as antiproliferative agents. The most potent analogues exhibited excellent cytotoxic activity against cancer cells while showing no toxicity to normal cells.
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, Organic
Robin Jeanneret, Carlo Walz, Maarten van Meerbeek, Sarah Coppock, M. Carmen Galan
Summary: A new practical, catalytic, and highly stereoselective method for directly accessing 1,1-alpha,alpha'-linked 2-deoxy trehalose analogues via AuCl3-catalyzed dehydrative glycosylation using hemiacetal glycosyl donors and acceptors is described. The method relies on the chemoselective Bronsted acid-type activation of tribenzylated 2-deoxy hemiacetals in the presence of other less reactive hemiacetals.
Article
Chemistry, Organic
Peiyun Jiang, Bingwei Hu, Xu Yuan, Jimei Yang, Xingjiang Yang, Jun Lin, Yi Jin
Summary: In this study, we report a sulfur-promoted reaction method that selectively synthesizes 2-aminofurans and 2-aminothiophenes from corresponding enaminones and methylene nitriles. The method is feasible, uses readily available starting materials, does not require transition metal catalysts, and has good tolerance for functional groups.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Zhen-yu Lu, Wei-qiao Lan, Fang-yi Liu, Jun-yi Wang, Xiao-mei Zhang, Li-hua Liao
Summary: An efficient catalytic asymmetric [3 + 2] cyclization of 3-substituted indoles with p-benzoquinones has been achieved using binol-chiral phosphoric acid. A variety of C3 substituted benzofuroindolines compounds were synthesized in moderate to high yields (up to 91% yield) and excellent enantioselectivities (up to 94% ee).
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Jais Kurian, Muraleedharan K. Manheri
Summary: An efficient synthetic route to access highly substituted pyrrolo[1,2-a]quinoline-3,5-diones through Ag(I)-catalyzed cyclization of 4-Hydroxyquinolinyl-2-ynones is discussed. The method allows for easy access to a new class of therapeutically relevant compounds with fusion of quinolone and pyrrolone moieties. Factors increasing the nucleophilicity of quinoline nitrogen or Lewis acid-coordination of the ynone unit contribute to high yields in short reaction times. Tandem cyclization-arylation sequence using Pd(II) generated by oxidative addition of Pd(0) with aryl iodide can also be executed to obtain specific substitution patterns.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Lukas Janecky, Athanasios Markos, Blanka Klepetar, Petr Beier
Summary: 4-Aryl-5-allyl-N-fluoroalkyl-1,2,3-triazoles were synthesized through a three-component reaction of fluoroalkyl azides, copper acetylides, and allyl halides. These compounds underwent aluminum halide-mediated transformation to N-(4-halo-2-aryl-cyclopentenyl) imidoyl halides by cyclization of vinyl cation intermediates, followed by halide capture. The cyclic products could be further utilized for the synthesis of N-alkenyl amides, amidines, isoquinolines, and tetrazoles, or for the subsequent modification of the cyclopentene ring.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Sofia Kokkaliari, Kim Pham, Nargess Shahbazi, Laurent Calcul, Lukasz Wojtas, Nerida G. Wilson, Alexander D. Crawford, Bill J. Baker
Summary: Five new alkaloids have been isolated from the lipophilic extract of the Antarctic tunicate Synoicum sp. These alkaloids exhibit their bioactivity by inducing embryonic dysmorphology characterized by axis truncation, including previously reported meridianins and newly discovered australindolones and meridianin H.
Article
Chemistry, Multidisciplinary
Nan-Sheng Li, Joseph A. Piccirilli, Geoffrey L. Greene
Summary: We have reexamined the reported method for the synthesis of MIBE and identified a different product based on NMR and MS data.
Article
Biochemistry & Molecular Biology
Fengxi Li, Yaning Xu, Ciduo Wang, Chunyu Wang, Ruihong Zhao, Lei Wang
Summary: A green and efficient process for the synthesis of Indoles from 1,3-diketones with fumaronitrile was developed in this study. When using CRL as the catalyst, high yields and satisfactory regioselectivity of cyano-containing multi-substituted indoles could be obtained. This enzymatic method demonstrates the great potential for the synthesis of indoles and extends the application of enzyme in organic synthesis.
BIOORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
