Article
Chemistry, Multidisciplinary
Franz-Lucas Haut, Niklas J. Feichtinger, Immanuel Plangger, Lukas A. Wein, Mira Mueller, Tim-Niclas Streit, Klaus Wurst, Maren Podewitz, Thomas Magauer
Summary: This study presents a new synthetic approach to polysubstituted pyrroles using 2,5-dihydrothiophenes, with the ring-opening of the heterocycle providing access to a panel of 1,3-dienes that undergo pyrrole formation in the presence of inexpensive chloramine-T trihydrate. The reaction is conducted in an open flask at ambient temperatures and key intermediates can be isolated by carefully adjusting the electronics and sterics of the 1,3-diene precursor. DFT studies identified a reaction mechanism involving a 6 pi-electrocyclization of a sulfilimine intermediate followed by spontaneous ring-contraction to reveal the pyrrole skeleton.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Vasiliki Polychronidou, Anna Krupp, Carsten Strohmann, Andrey P. Antonchick
Summary: A metal-free protocol for the synthesis of substituted 1,6-dihydropyridines with quaternary stereogenic centers has been developed, demonstrating high functional group compatibility and broad scope. Modification of products allows for increased complexity and chemical diversity, with attempts at asymmetric synthesis shown.
Article
Chemistry, Organic
Li-Chun Lin, Sundaram Suresh, Kun-Wu Lin, Veerababurao Kavala, Ching-Fa Yao
Summary: We have developed a copper-catalyzed three-component reaction for the synthesis of disubstituted nicotinonitriles. This reaction involves the condensation of 3-bromopropenals with benzoylacetonitriles, followed by in situ generation of ammonia and transformation into trisubstituted pyridines via a reaction sequence involving 6π-azaelectrocyclization and aromatization.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Ivan E. Romero, Al Postigo, Sergio M. Bonesi
Summary: This review focuses on the synthesis of carbazole derivatives using various methods, such as direct irradiation, photosensitization, photoredox, electrochemical, and thermal cyclization reactions. The methods described in this review enable efficient formation of new C-C and C-heteroatom bonds under mild conditions and allow for broad substrate diversity and functional group tolerance.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Shuto Kosuge, Yusuke Araki, Kiyoshi Tsuge, Kenji Sugimoto, Yuji Matsuya
Summary: The one-pot de novo synthesis of pentasubstituted pyridines is achieved through Au-(I)-autotandem catalysis and subsequent aromatization. This process involves aza-enyne metathesis with aryl propiolates to yield 1-azabutadienes and their addition/6 pi-electrocyclization sequence with the other propiolate units. The resulting 1,4-dihydropyridines are aromatized to produce pyridines in the presence of atmospheric oxygen. The aryl propiolates are regioselectively incorporated into the ring system, leading to the formation of 2-arylpyridines as the sole product.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Robert F. Lusi, Goh Sennari, Richmond Sarpong
Summary: A strategy orthogonal to classic approaches and coupled with C-H functionalization methods has been used to achieve the shortest synthesis and divergent syntheses of a sesquiterpenoid longiborneol, providing inspiration for the synthesis of other topologically complex natural products.
Article
Chemistry, Organic
Jagmeet Singh, Pargat Singh, Mahendra Nath
Summary: Novelnickel-(II) and copper-(II) complexes of 2-(N,N-dimethylformamidine)-3-formyl-5,10,15,20-tetraarylporphyrins were synthesized for the first time using Vilsmeier-Haack conditions. These porphyrins were then used as building blocks to construct diverse β-pyrimidine-fused 5,10,15,20-tetraarylporphyrins in good yields through a cascade ammonia-mediated condensation and intramolecular aza-6 π-annulation/aromatization in 1,2-dichloroethane at 80°C. Additionally, copper-(II) β-pyrimidine-fused porphyrins underwent demetallation in the presence of conc. H2SO4 to afford free-base porphyrins, which were further inserted with zinc to obtain zinc-(II) β-pyrimidine-fused porphyrins.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jagmeet Singh, Pargat Singh, Mahendra Nath
Summary: Novelnickel-(II) and copper-(II) complexes of 2-(N,N-dimethylformamidine)-3-formyl-5,10,15,20-tetraarylporphyrins have been synthesized for the first time from 2-aminoporphyrins under Vilsmeier-Haack conditions. These porphyrins are utilized as new building blocks to construct diverse beta-pyrimidine-fused 5,10,15,20-tetraarylporphyrins in good yields via a cascade ammonia-mediated condensation and intramolecular aza-6 pi-annulation/aromatization in 1,2-dichloroethane at 80 degrees C. Furthermore, copper-(II) beta-pyrimidine-fused porphyrins underwent demetallation in the presence of conc. H2SO4 to afford free-base porphyrins, which on zinc insertion using Zn-(OAc)(2) in CHCl3-MeOH provided zinc-(II) beta-pyrimidine-fused porphyrins in appreciable yields. Notably, these newly synthesized pi-extended porphyrins displayed a modest bathochromic shift in their electronic absorption and emission spectra as compared to the traditional meso-tetraarylporphyrins. However, the protonated porphyrins (2a) and (3g) displayed a significant red-shifted absorption.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Turan T. Karibov, Boris Lichitsky, Valeriya G. Melekhina, Andrey N. Komogortsev
Summary: The photochemical behavior of terarylenes containing benzofuran and aminopyrazole fragments was studied. It was found that the presence of an amino group in the structure of the studied terarylenes blocks photocyclization, but the transformation of the amino group into a pyrrole fragment allows one to remove the aforementioned blocking effect.
POLYCYCLIC AROMATIC COMPOUNDS
(2023)
Article
Chemistry, Multidisciplinary
Hao-Yuan Liu, Zhen-Yu Zhang, Yi-Ke Zhou, Jia-Hua Chen, Zhen Yang, Yuan-He Li
Summary: This paper presents an efficient strategy for synthesizing the DEFGH rings of phainanoid F, involving a photo-induced electrocyclization and a homoallylic elimination. It is noteworthy that the electrocyclization reaction was used to simultaneously construct two vicinal quaternary carbons in total synthesis, which is a rare example. The strategy outlined here serves as the basis for the total synthesis of Phainanoid F and could be applied in synthesizing other natural products with similar 13,30-cyclodammarane skeletons.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Multidisciplinary Sciences
Wen Chen, Yonghui Ma, Wenyan He, Yinxia Wu, Yuancheng Huang, Yipeng Zhang, Hongchang Tian, Kai Wei, Xiaodong Yang, Hongbin Zhang
Summary: The authors report a unified approach towards the asymmetric synthesis of Sarpagine-Ajmaline-Koumine type alkaloids, leading to the synthesis of 14 natural alkaloids. These alkaloids have significant biological activities.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Hamza Majeed Ansari, Weijia Wang, Lin Lei, Kuo Bao, Xinye Chang, Ali Raza, Yongfeng Chen, Asad Mehboob, Qi Zhong, Anurag Srivastava, Olga Kaimieva, Huiqing Fan
Summary: In this study, ultra-thin 2D g-C3N4 nanosheets were successfully self-assembled into a large-scale 3D macroporous structure with the assistance of NH4Cl through a gas bubbling exfoliation strategy. The doping of N and Cl was achieved during synthesis. The resulting hierarchical structure exhibited remarkable improvement in photocatalytic water reduction reaction.
JOURNAL OF ALLOYS AND COMPOUNDS
(2022)
Article
Oncology
Deborah Mackay, Jet Bliek, Masayo Kagami, Jair Tenorio-Castano, Arrate Pereda, Frederic Brioude, Irene Netchine, Dzhoy Papingi, Elisa de Franco, Margaret Lever, Julie Sillibourne, Paola Lombardi, Veronique Gaston, Maithe Tauber, Gwenaelle Diene, Eric Bieth, Luis Fernandez, Julian Nevado, Zeynep Tumer, Andrea Riccio, Eamonn R. Maher, Jasmin Beygo, Pierpaola Tannorella, Silvia Russo, Guiomar Perez de Nanclares, I. Karen Temple, Tsutomu Ogata, Pablo Lapunzina, Thomas Eggermann
Summary: Imprinting disorders, which are caused by genetic or epigenetic changes, can affect various aspects including growth, development, metabolism, and risk of neoplasia. Current diagnostic methods involve analyzing gene dosage and methylation, and some laboratories also use multi-locus testing. Our investigation into different testing strategies revealed their impact on diagnostic outcomes.
CLINICAL EPIGENETICS
(2022)
Review
Chemistry, Organic
Xuchen Zhao, Jon D. Rainier
Summary: This review focuses on the photoelectrocyclization of conjugated vinyl biaryls as a valuable strategy for generating phenanthrene derivatives. It provides an overview of the transformation mechanism, discusses the reaction scope, and highlights the application of the reaction in natural product synthesis.
SYNTHESIS-STUTTGART
(2021)
Article
Engineering, Environmental
Ke-Ying Tao, Kuo Yuan, Wei Yang, Di-Chang Zhong, Tong-Bu Lu
Summary: In this study, C-NHx-rich g-C3N4 photocatalysts were prepared by a template co-pyrolysis strategy, which increased the CO2 binding and improved the photocatalytic CO2 reduction efficiency by enhancing the capacity of CO2 capture and optimizing the separation of photo-generated electron and hole. The C-NHx-rich g-C3N4 exhibited greatly enhanced photocatalytic activity for CO2RR, over 74-fold higher than that of conventionally prepared g-C3N4, providing a new avenue for optimizing g-C3N4-based photocatalysts for CO2RR.
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Chemistry, Organic
Juan A. Gil, Fabio Arias, Rachid Chahboun, Enrique Alvarez-Manzaneda
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Environmental Sciences
Ines Aguilar-Romero, Jesus De la Torre-Zuniga, Jose Miguel Quesada, Ali Haidour, Garret O'Connell, Breanne M. McAmmond, Jonathan D. Van Hamme, Esperanza Romero, Regina-Michaela Wittich, Pieter van Dillewijn
Summary: The study on the ibuprofen-mineralizing bacterial strain RW412 isolated from sediments of the River Elbe showed that it can eliminate more than 2 mM ibuprofen within 74 hours in liquid mineral salts medium, and quickly remove ibuprofen in biopurification systems as well.
ENVIRONMENTAL POLLUTION
(2021)
Article
Plant Sciences
Ruben Martin-Escolano, Juan J. Guardia, Javier Martin-Escolano, Nuria Cirauqui, Antonio Fernandez, Maria J. Rosales, Rachid Chahboun, Manuel Sanchez-Moreno, Enrique Alvarez-Manzaneda, Clotilde Marin
JOURNAL OF NATURAL PRODUCTS
(2020)
Article
Chemistry, Physical
Ayoub Abdelkader Mekkaoui, Hicham Ben El Ayouchia, Hafid Anane, Rachid Chahboun, Larbi El Firdoussi, Soufiane El Houssame
Summary: A novel, efficient synthesis pathway for optically active limonaketone was developed, starting from limonene, with an overall yield of 84%. The strategy involved a three-step total synthesis of limonaketone, a potentially important intermediate in limonene ozonolysis. By utilizing density functional theory calculations, the chemoselectivity in the Zn-deoxygenation reaction and its mechanistic pathway were elucidated.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Environmental Sciences
Irene Calvente, Maria Isabel Nunez, Rachid Chahboun Karimi, Juan Villalba-Moreno
Summary: The pilot study found that there were differences in radon concentrations in workplaces in three buildings of Granada University constructed in different centuries, with ventilation being a key factor in reducing radon levels.
INTERNATIONAL JOURNAL OF ENVIRONMENTAL RESEARCH AND PUBLIC HEALTH
(2021)
Article
Chemistry, Organic
Rachid Chahboun, Jose Manuel Botubol-Ares, Maria Jesus Duran-Pena, Fermin Jimenez, Ramon Alvarez-Manzaneda, Enrique Alvarez-Manzaneda
Summary: This study presents a general and efficient method for the deconjugative alpha-alkylation of alpha,beta-unsaturated aldehydes under mild conditions through a synergistic effect between (BuOK)-Bu-t and NaH. The resulting beta,gamma-unsaturated aldehyde can be transformed into the corresponding allyl acetate via lead(IV) acetate-mediated oxidative fragmentation, with high yield. This strategy is applicable for constructing the carbon skeleton of diverse alkyl or aryl terpenoids.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Christian A. Celaya, Rachid Oukhrib, Mustapha Ait El Had, Youness Abdellaoui, Hicham Abou Oualid, Hassane Bourzi, Rachid Chahboun, Deyang Zhao, Sameh M. Osman, Virinder S. Parmar, Christophe Len
MOLECULAR CATALYSIS
(2022)
Article
Plant Sciences
Houda Zentar, Fatin Jannus, Pilar Gutierrez, Marta Medina-O'Donnell, Jose Antonio Lupianez, Fernando J. Reyes-Zurita, Enrique Alvarez-Manzaneda, Rachid Chahboun
Summary: A new strategy for the semisynthesis of the aromatic cassane-type diterpene taepeenin F (6) is reported, which showed potential antiproliferative activity against tumor cell lines and anti-inflammatory effects. Salicylaldehyde 21 was identified as the most active compound, inducing apoptosis in tumor cells and inhibiting inflammatory response.
JOURNAL OF NATURAL PRODUCTS
(2022)
Article
Biochemistry & Molecular Biology
Houda Zentar, Fatin Jannus, Marta Medina-O'Donnell, Jose A. Lupianez, Jose Justicia, Ramon Alvarez-Manzaneda, Fernando J. Reyes-Zurita, Enrique Alvarez-Manzaneda, Rachid Chahboun
Summary: A set of cassane-type diterpenes were synthesized and their anti-inflammatory and anti-cancer activities were evaluated. Some compounds showed high anti-inflammatory activity and cytotoxicity in cell lines.
Article
Chemistry, Medicinal
Fatima I. I. Mahi, Mohammed A. A. Mehdid, Houda Zentar, Adil A. A. Othman, Az-eddine El Mansouri, Nisserine Hamini-Kadar, Fernando J. J. Reyes-Zurita, Rachid Chahboun
Summary: Two main products, 18-hydroxy-cis-clerodan-3-ene-15-oic acid and 18-acetoxy-cis-clerodan-3-ene-15-oic acid, were isolated from the plant Cistus monspeliensis. The 18-acetoxy acid was converted to its mother 18-hydroxy acid in good yield. The synthesized 1,3,4-oxadiazole derivatives showed interesting antioxidant and antibacterial activities, as well as higher anti-inflammatory effects compared to the reference compound.
MEDICINAL CHEMISTRY RESEARCH
(2023)
Article
Biochemistry & Molecular Biology
Juan J. J. Guardia, Antonio Fernandez, Jose Justicia, Houda Zentar, Ramon Alvarez-Manzaneda, Enrique Alvarez-Manzaneda, Rachid Chahboun
Summary: The acid treatment of 6,7-seco-abietane dialdehydes leads to the synthesis of derivatives with the 4a-methyltetrahydrofluorene skeleton of taiwaniaquinoids in high yield. The proposed mechanism involves the elimination of formic acid from the cyclic aldol intermediate. This novel reaction enables the enantiospecific synthesis of bioactive natural cupresol and taxodal.
Article
Medicine, Research & Experimental
Nuria Mut-Salud, Juan J. Guardia, Antonio Fernandez, Isabel Blancas, Houda Zentar, Jose M. Garrido, Enrique Alvarez-Manzaneda, Rachid Chahboun, Fernando Rodriguez-Serrano
Summary: In this study, the antitumor activity of taiwaniaquinoids, specifically compound C36, was investigated in vitro and in vivo. Results showed that C36 exhibited significant antitumor effects on MCF-7 cells by inducing apoptosis through caspase 9 activation and an increase in the Bax/Bcl-2 ratio. In vivo experiments also demonstrated the efficacy of C36 in reducing tumor growth and improving survival rates in immune-competent C57BL/6 mice implanted with E0771 mouse mammary tumor cells.
BIOMEDICINE & PHARMACOTHERAPY
(2023)
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
