Article
Chemistry, Organic
Sydney N. Jackson, Andrew L. Caskey, Natasha K. Narayanan, Bradley L. Merner
Summary: The attempted dehydration of macrocyclic alpha-ketols with the Burgess reagent unexpectedly resulted in the synthesis of carbamoylated, bent para-phenylene units, while the same reaction with an acyclic analogue produced the intended dehydration product, suggesting that the change in reactivity is conformationally controlled and a result of the bifunctional nature of the Burgess reagent.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Kouki Fuchino, Moriyasu Masui, Shuhei Yoshida, Ken-ichi Kusakabe
Summary: A cyclization reaction was developed to access amino-1,3-oxazines under mild conditions using dehydrating reagents. The reaction tolerated labile functional groups and can be utilized for synthesizing BACE1 inhibitors with a variety of warheads.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Michal Ociepa, Kyle W. Knouse, David He, Julien C. Vantourout, Dillon T. Flood, Natalia M. Padial, Jason S. Chen, Brittany B. Sanchez, Emily J. Sturgell, Bin Zheng, Shenjie Qiu, Michael A. Schmidt, Martin D. Eastgate, Phil S. Baran
Summary: An operationally simple, scalable, and chemoselective method for the direct phosphorylation of alcohols has been developed, using a P(V)-approach based on the Psi-reagent platform. The method has a broad substrate scope and can be applied in both simple and complex settings, providing access to valuable phosphorylated alcohols that would be difficult to obtain otherwise.
Article
Chemistry, Multidisciplinary
Frederic Aribot, Amelie Merle, Pierre Dechambenoit, Harald Bock, Albert Artigas, Nicolas Vanthuyne, Yannick Carissan, Denis Hagebaum-Reignier, Yoann Coquerel, Fabien Durola
Summary: A rigid propeller-shaped conjugated triple macrocycle has been synthesized, consisting of two stacked benzene rings and three linking [5]helicene moieties, using a glyoxylic Perkin approach. Electron delocalization analysis of this atypical aromatic molecule revealed global aromaticity, with a 78 pi-electron circuit along the edge of its triple loop, at the expense of the two 6 pi-electron circuits in the stacked benzene rings.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Anastasiya V. Agafonova, Artem A. Golubev, Ilia A. Smetanin, Alexander F. Khlebnikov, Dar'ya V. Spiridonova, Mikhail S. Novikov
Summary: This article describes the reactions of 2-(2-pyridyl)azirines under different catalysts, in which the N-C2 bond is selectively cleaved under copper(II) catalysis, and the C-C bond is cleaved under the action of HCl, resulting in different reaction products.
Article
Chemistry, Multidisciplinary
Hongmei Jiang, Haicheng Shen, Sha Zhu, Binbin Wang, Yujie Yang, Zhibin Nong, Min Yi, Shiyun Tang, Qing-Wen Gui
Summary: A novel and inexpensive double thiolation reagent has been reported for sulfurizing a broad range of imidazo[1,2-alpha]pyridines under mild conditions. Diethylaminosulfur trifluoride, a common nucleophilic fluorinating reagent, was utilized as the novel thiolation reagent in this study.
Article
Chemistry, Organic
Michael G. Darnowski, Taylor D. Lanosky, Andre R. Paquette, Christopher N. Boddy
Summary: This study focuses on the synthesis of a unique natural product armeniaspirol and the discovery of a new reaction that rapidly generates the desired structure. By expanding the scope of this oxidation reaction, a series of similar compounds were successfully synthesized, among which pseudoarmeniaspirol shows antibiotic activity but with lower bioactivity compared to the natural product.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Ali Nikbakht, Ahmadreza Ebrahimi Valdani, Hossein Zahedian Tejeneki, Alireza Abbasi Kejani, Nahid S. Alavijeh, Felix Bauer, Fatemeh Darvish, Bernhard Breit, Saeed Balalaie
Summary: A diastereoselective cascade annulation between allenoates and in-situ generated isoquinoline N-oxides is reported, leading to the formation of sp3-rich bridged polycyclic heterocycles through an unprecedented non-rearomatized rearrangement. The reaction exhibits high diastereoselectivity and good functional group tolerance, achieving yields of 38-93%. Density functional theory calculations offer insights into the reaction pathway and stereoselectivity.
Article
Food Science & Technology
William R. Kem, James R. Rocca, Jodie V. Johnson, Juan Junoy
Summary: Nemerteans are marine worms that utilize toxins for prey capture and self-defense. Hoplonemerteans, divided into Monostilifera and Polystilifera, have proboscises armed with stylets. Many monostiliferans contain alkaloidal toxins, such as anabaseine, which have various effects on different receptors and can reduce predation and larval settlement. Anabaseine has potential therapeutic applications for Alzheimer's disease and schizophrenia due to its interaction with nicotinic acetylcholine receptors.
Letter
Chemistry, Organic
Xiang-Long Chen, Dong-Sheng Yang, Bo-Cheng Tang, Chun-Yan Wu, Huai-Yu Wang, Jin-Tian Ma, Shi-Yi Zhuang, Zhi-Cheng Yu, Yan-Dong Wu, An-Xin Wu
Summary: A concise and efficient hydrodefluorination process using rongalite as a masked proton source has been developed for the synthesis of gem-difluoroalkenes. No additional catalysts or reductants are required, and both terminal and internal double bonds in trifluoromethyl alkenes are compatible with this process, enabling a wider range of substrates. Successful late-stage functionalizations of pharmaceuticals and gram-scale syntheses demonstrate the viability of this method.
Review
Chemistry, Multidisciplinary
Jasmine Panda, Bishnu P. Raiguru, Mitali Mishra, Seetaram Mohapatra, Sabita Nayak
Summary: This review summarizes recent synthetic pathways of imidazo[1,2-a]pyridines, including transition metal-catalyzed reactions, multi-component reactions, and other innovative synthesis strategies.
Article
Chemistry, Organic
Asim Swain, Prince Ravat
Summary: High luminescence quantum yield and dissymmetric factors are crucial for the development of circularly polarized materials utilizing helicene-embedded polycyclic aromatic hydrocarbons to enhance their (chir)optical properties. The fusing mode and molecular symmetry greatly influence the (chir)optical properties of pyrene fused mono helicenes. In this study, we report on the stereospecific synthesis and (chir)optical properties of C-1 symmetric pyrene fused double [7]helicene, which exhibited higher absorption and emission dissymmetric factors and a significant increase in fluorescence quantum yield compared to single helicene congeners. These findings provide further insights into the effect of molecular symmetry on the (chir)optical properties of helicenes.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Review
Chemistry, Organic
Vikrant V. Kumbhar, Bhushan B. Khairnar, Manohar G. Chaskar, Ramdas A. Pawar, Gulab S. Gugale
Summary: Imidazo[1,2-a]pyridines are important nitrogen-containing heterocyclic scaffolds with wide applications in medicinal chemistry, organometallics, and material science. This review discusses the rigorous efforts made in the past decade towards the regioselective and straightforward synthesis of 3-aroyl and 2-aroyl imidazo[1,2-a]pyridines, as well as highlights the challenges in achieving regioselective aroylation at the C-2 position.
SYNTHETIC COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Yuqin Dou, Xin Yang, Qi Wang, Zhaodi Yang, Aijian Wang, Long Zhao, Weihua Zhu
Summary: In this study, a novel cobalt porphyrin (CoTAPP)-bridged covalent triazine polymer (CoTAPPCC) was prepared for electrocatalytic hydrogen evolution reaction (HER) by covalently linking CoTAPP with cyanuric chloride (CC). Experimental techniques and density functional theory (DFT) calculations were used to evaluate the correlation of HER activity with molecular structures. The strong electronic interactions between the CC unit and the CoTAPP moiety result in a standard current density of 10 mA cm-2 with a low overpotential of 150 mV in acid, which is comparable to or better than the best records reported previously. Additionally, CoTAPPCC exhibits competitive HER activity in basic medium. This strategy is valuable for designing and developing efficient porphyrin-based HER electrocatalysts.
JOURNAL OF COLLOID AND INTERFACE SCIENCE
(2023)
Review
Chemistry, Multidisciplinary
Jasmine Panda, Bishnu P. P. Raiguru, Mitali Mishra, Seetaram Mohapatra, Sabita Nayak
Summary: This review provides a comprehensive overview of the recent synthetic pathways of imidazo[1,2-a]pyridines, including transition metal-catalyzed reactions, multi-component reactions, cyclization, condensation, microwave-assisted reactions, heteroannular and photocatalytic reactions. Imidazo[1,2-a]pyridines are privileged heterocyclic structures widely found in natural products. The review summarizes the recent advances in their synthesis from various substrates from 2016 to 2021 and discusses the challenges associated with the reported methods.
Article
Pharmacology & Pharmacy
Ranjan Mukherjee, Kenneth T. Locke, Bowman Miao, Daniel Meyers, Hossain Monshizadegan, Rongan Zhang, Debra Search, Denise Grimm, Michael Flynn, Kevin M. O'Malley, Litao Zhang, Jun Li, Yan Shi, Lawrence J. Kennedy, Michael Blanar, Peter T. Cheng, Joseph Tino, Rai Ajit Srivastava
JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS
(2008)
Article
Chemistry, Organic
Lawrence J. Kennedy
Article
Chemistry, Organic
Lawrence J. Kennedy
TETRAHEDRON LETTERS
(2010)
Article
Chemistry, Medicinal
Yan Shi, Doree Sitkoff, Jing Zhang, Wei Han, Zilun Hu, Philip D. Stein, Ying Wang, Lawrence J. Kennedy, Stephen P. O'Connor, Saleem Ahmad, Eddie C. -K. Liu, Steve M. Seller, Patrick Y. S. Lam, Jeffrey A. Robl, John E. Macor, Karnail S. Atwal, Robert Zahler
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2007)
Article
Chemistry, Multidisciplinary
PA Evans, LJ Kennedy
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2001)
Article
Chemistry, Organic
PA Evans, LJ Kennedy