Article
Chemistry, Organic
Zhi Zhang, Jing-Tong Deng, Jia-Yi Feng, Jin-Yan Liang, Xue-Tao Xu, Jin-Bao Peng
Summary: A palladium-catalyzed annulation of o-iodo-anilines with propargyl alcohols for the synthesis of substituted quinolines has been developed. The reaction shows tolerance towards diverse functional groups under mild conditions, providing a direct access to 2,4-disubstituted quinolines from easily available starting materials. A broad range of 2,4-disubstituted quinolines were efficiently synthesized in good to excellent yields.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Xiaohui Wei, Xuewu Liang, Yazhou Li, Qi Liu, Xuyi Liu, Yu Zhou, Hong Liu
Summary: The study introduces a metal-free and environmentally friendly approach for the intramolecular cascade cyclization and dearomatization of indole derivatives, which selectively produce iodinated and vinylic spiroindolenines through a substrate-controlled strategy. The simplicity of operation, mild conditions, and high yield make this method a green and attractive pathway to generate functionalizable spiroindolenine scaffolds that can be converted into diverse useful derivatives.
Article
Chemistry, Organic
Jiangjie Zhang, Shangyuan Wang, Jian-Shu Wang, Jun Ying, Xiao-Feng Wu
Summary: A palladium-catalyzed carbonylative cyclization of 2-ethynylanilines with nitroarenes has been developed for the rapid synthesis of indole-3-carboxamide skeletons. The reaction proceeded smoothly to furnish various indole-3-carboxamide derivatives in moderate to high yields by using nitroarenes as the nitrogen source and Mo(CO)(6) as the CO surrogate.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Dong Tang, Yangxiu Mu, Zafar Iqbal, Lili He, Rui Jiang, Jing Hou, Zhixiang Yang, Minghua Yang
Summary: An efficient protocol has been developed for the synthesis of pyrazolo[4,3-c]quinoline derivatives using (1H-pyrazol-5-yl)anilines and readily available alcohols/amines. The strategy successfully converted a wide range of substrates with diverse functional groups to the corresponding products in moderate to good yields under optimal reaction conditions, and also showed compatibility with thiol and amino acid for accessing pyrazolo[4,3-c]quinoline derivatives.
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Grant J. Sherborne, Paul Kemmitt, Callum Prentice, Eli Zysman-Colman, Andrew D. Smith, Charlene Fallan
Summary: This study developed a light-mediated cyclisation method for the selective synthesis of tetrahydroquinolines or quinoline derivatives. The method is efficient, atom economical, and tolerant to functional groups, including azaarene-bearing substrates.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Zhimin Sun, Mengfu Dai, Chencheng Ding, Shiqin Chen, Liang-An Chen
Summary: We have developed a catalyst-controlled regiodivergent method for synthesizing structurally diverse 1,2,3,4-tetrasubstituted conjugated dienes. This method uses readily available propargyl esters and diaryliodonium salts and achieves excellent regio- and stereochemical outcomes. The unique feature of this method is the use of an in situ generated highly electrophilic aryl-Cu-III complex as both a π-Lewis acid catalyst for alkyne activation/acyloxy migration and an aryl electrophile equivalent. The competitive arylative 1,2- and 1,3-acyloxy migration patterns are controlled by Cu and Au/Cu relay catalyses, enabling the synthesis of traditionally inaccessible tetrasubstituted 1,3-dienes in a regiodivergent manner. The versatility of this method is demonstrated by its further application in the synthesis of a range of useful compounds.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Si Deng, Wenliang Ouyang, Jiang Bai, Xian-Rong Song, Ruchun Yang, Qiang Xiao
Summary: A new and convenient protocol is presented for the synthesis of 3,6,8-tribromoquinolines via cascade cyclization of N-(3-phenylprop-2-ynyl)anilines using N-bromosuccinimide as an electrophile. The metal-free process is carried out under mild conditions and is compatible with various substituents. The Sonogashira coupling reaction regioselectively occurs at position C-6 of the obtained products.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Anton S. Makarov, Arthur N. Bakiev, Diana A. Eshmemeteva
Summary: We present a metal- and additive-free method for synthesizing meta-substituted anilines using commercially available or one-step accessible substituted methylvinyl ketones, N-acylpyridinium salts, and primary/secondary alkyl- and arylamines. This method enables the synthesis of anilines with uncommon substitution patterns and has potential applications in medicinal chemistry and materials science.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Hayden D. Bishop, Qiang Zhao, Christopher Uyeda
Summary: Transition-metal-catalyzed reductive coupling reactions of alkynes and imines are attractive methods for the synthesis of chiral allylic amines. In this study, an alternative pathway involving transmetalation to zinc was discovered, and the versatile application of organozinc product in carbon-carbon and carbon-heteroatom coupling reactions was demonstrated.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Applied
Joana C. Lopes, Tania Moniz, Maria J. Sampaio, Claudia G. Silvia, Maria Rangel, Joaquim L. Faria
Summary: In this study, a metal-free exfoliated carbon nitride (GCN-T) catalyst was used for the oxidative self-coupling of benzylamine (BZA) under visible light irradiation. The reaction achieved complete conversion of BZA and 97% selectivity towards N-benzylidenebenzylamine (BZI) production. Electron paramagnetic resonance (EPR) spectroscopy revealed the involvement of superoxide and singlet oxygen radicals in the photocatalytic mechanism. A reaction pathway was proposed to explain the observed results. These findings contribute to the development of customizable heterogeneous photocatalytic solutions for efficient solar synthesis.
Article
Chemistry, Physical
Douglas J. Fansher, Richard Granger, Satinderpal Kaur, David R. J. Palmer
Summary: The chemoenzymatic synthesis of quinaldic acids under mild conditions using an aldolase resulted in up to 93% isolated yield. This reaction differs from aldol condensation catalyzed by NahE in vivo, resembling the heterocycle formation catalyzed by its homologue instead.
Article
Chemistry, Organic
Chungang Li, Mingli Zhong, Zheng Zeng, Yiqiu Deng, Lanyu Li
Summary: An iridium-catalyzed hydrogen transfer strategy allows for the straightforward synthesis of tetrahydropyridine derivatives, offering high efficiency and environmental friendliness.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Lauren G. O'Neil, John F. Bower
Summary: Classical amination methods involve the reaction of a nitrogen nucleophile with an electrophilic carbon center; however, in recent years, umpoled strategies have gained traction where the nitrogen source acts as an electrophile. A wide range of electrophilic aminating agents are now available, and these underpin a range of powerful C-N bond-forming processes. In this Review, we highlight the strategic use of electrophilic aminating agents in total synthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Aya Saito, Kazuhiro Yoshida, Hideo Togo
Summary: Treatment of N-propargyl-N'-tosylhydrazines with molecular iodine (I-2) in the presence of NaHCO3 under warming conditions efficiently afforded the corresponding 5-substituted 4-iodo-1-tosylpyrazoles, while the same reaction in the presence of acetic acid generated the corresponding 5-aryl-4-iodopyrazoles.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Nicola Zanda, Leijie Zhou, Esther Alza, Arjan W. Kleij, Miquel A. Pericas
Summary: The article presents an efficient synthesis method using TBD catalyst to convert epoxy amines to 2-oxazolidone, combining the use of CO2 as a C-1 source and halide-free organocatalysis to continuously synthesize a series of heterocyclic products over a two-week period.
Article
Environmental Sciences
Patricia A. Janulewicz, Ratanesh K. Seth, Jeffrey M. Carlson, Joy Ajama, Emily Quinn, Timothy Heeren, Nancy Klimas, Steven M. Lasley, Ronnie D. Horner, Kimberly Sullivan, Saurabh Chatterjee
INTERNATIONAL JOURNAL OF ENVIRONMENTAL RESEARCH AND PUBLIC HEALTH
(2019)
Article
Environmental Sciences
Sutapa Sarkar, Firas Alhasson, Diana Kimono, Muayad Albadrani, Ratanesh K. Seth, Shuo Xiao, Dwayne E. Porter, Geoff I. Scott, Bryan Brooks, Mitzi Nagarkatti, Prakash Nagarkatti, Saurabh Chatterjee
ENVIRONMENTAL TOXICOLOGY AND PHARMACOLOGY
(2020)
Meeting Abstract
Biochemistry & Molecular Biology
Ayan Mondal, Ratanesh Seth, Dipro Bose, Mitzi Nagarkatti, Prakash Nagarkatti, Saurabh Chatterjee
Meeting Abstract
Biochemistry & Molecular Biology
Ayan Mondal, Ratanesh Seth, Sutapa Sarkar, Dipro Bose, Punnag Saha, Diana Kimono, Muayad Albadrani, Mitzi Nagarkatti, Prakash Nagarkatti, Saurabh Chatterjee
Article
Biochemistry & Molecular Biology
Sutapa Sarkar, Punnag Saha, Ratanesh K. Seth, Ayan Mondal, Dipro Bose, Diana Kimono, Muayad Albadrani, Avik Mukherjee, Dwayne E. Porter, Geoff I. Scott, Shuo Xiao, Bryan Brooks, John Ferry, Mitzi Nagarkatti, Prakash Nagarkatti, Saurabh Chatterjee
COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY C-TOXICOLOGY & PHARMACOLOGY
(2020)
Article
Immunology
Ayan Mondal, Dipro Bose, Punnag Saha, Sutapa Sarkar, Ratanesh Seth, Diana Kimono, Muayad Albadrani, Mitzi Nagarkatti, Prakash Nagarkatti, Saurabh Chatterjee
JOURNAL OF NEUROINFLAMMATION
(2020)
Article
Neurosciences
Dipro Bose, Ayan Mondal, Punnag Saha, Diana Kimono, Sutapa Sarkar, Ratanesh K. Seth, Patricia Janulewicz, Kimberly Sullivan, Ronnie Horner, Nancy Klimas, Mitzi Nagarkatti, Prakash Nagarkatti, Saurabh Chatterjee
Article
Nutrition & Dietetics
Dipro Bose, Punnag Saha, Ayan Mondal, Brian Fanelli, Ratanesh K. Seth, Patricia Janulewicz, Kimberly Sullivan, Stephen Lasley, Ronnie Horner, Rita R. Colwell, Ashok K. Shetty, Nancy Klimas, Saurabh Chatterjee
Article
Chemistry, Multidisciplinary
Grace P. Ahlqvist, Catherine P. McGeough, Chris Senanayake, Joseph D. Armstrong, Ajay Yadaw, Sarabindu Roy, Saeed Ahmad, David R. Snead, Timothy F. Jamison
Summary: A supply-centered and chromatography-free synthesis of molnupiravir from cytidine has been successfully described, with an improved overall isolated yield compared to the patented route; this new route has the potential to reduce the production cost of the drug.
Article
Neurosciences
Punnag Saha, Peter T. Skidmore, LaRinda A. Holland, Ayan Mondal, Dipro Bose, Ratanesh K. Seth, Kimberly Sullivan, Patricia A. Janulewicz, Ronnie Horner, Nancy Klimas, Mitzi Nagarkatti, Prakash Nagarkatti, Efrem S. Lim, Saurabh Chatterjee
Summary: The study demonstrates that treatment with andrographolide can significantly improve Gut-Brain axis-related pathology in a mouse model of GWI, potentially providing a much-needed therapeutic avenue for this condition.
Article
Chemistry, Applied
Sarabindu Roy, Ajay Yadaw, Subho Roy, Gopal Sirasani, Aravind Gangu, Jack D. Brown, Joseph D. Armstrong, Rodger W. Stringham, B. Frank Gupton, Chris H. Senanayake, David R. Snead
Summary: This study presents a newly developed synthetic methodology for the production of Pyrrolo[2,1-f][1,2,4]triazine, an important starting material for the antiviral drug remdesivir. Through examining the mechanistic pathway, simple building blocks such as pyrrole, chloramine, and formamidine acetate were successfully utilized to obtain triazine 1 with an overall yield of 55% in a two-vessel-operated process. The research also focuses on the safety of the process, impurity profiles and control, and efforts towards scale-up for large-scale production.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Chemistry, Applied
Vijayagopal Gopalsamuthiram, Appasaheb L. Kadam, Jeffrey K. Noble, David R. Snead, Corshai Williams, Timothy F. Jamison, Chris Senanayake, Ajay K. Yadaw, Sarabindu Roy, Gopal Sirasani, B. Frank Gupton, Justina Burns, Daniel W. Cook, Rodger W. Stringham, Saeed Ahmad, Rudy Krack
Summary: A scalable four-step synthesis of molnupiravir from cytidine is described, utilizing inexpensive reagents and environmentally friendly solvents. The improved isolation and purification procedures allow for high purity product to be obtained. Key steps in the synthesis were carried out on a multigram scale to afford molnupiravir with high purity levels.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Meeting Abstract
Immunology
Ratanesh K. Seth, Dipro Bose, Punnag Saha, Diana Kimono, Ayan Mondal, Patricia Janulewicz Lloyd, Nancy Klimas, Ronnie D. Horner, Kimberly Sullivan, Efrem S. Lim, Mitzi Nagarkatti, Prakash S. Nagarkatti, Saurabh Chatterjee
JOURNAL OF IMMUNOLOGY
(2020)
Article
Environmental Sciences
Muayad Al-Badrani, Punnag Saha, Ayan Mondal, Ratanesh K. Seth, Sutapa Sarkar, Diana Kimono, Dipro Bose, Dwayne E. Porter, Geoff Scott, Bryan Brooks, Samir Raychoudhury, Mitzi Nagarkatti, Prakash Nagarkatti, Saurabh Chatterjee
ENVIRONMENTAL TOXICOLOGY AND PHARMACOLOGY
(2020)
Article
Neurosciences
Diana Kimono, Dipro Bose, Ratanesh K. Seth, Ayan Mondal, Punnag Saha, Patricia Janulewicz, Kimberly Sullivan, Stephen Lasley, Ronnie Horner, Nancy Klimas, Saurabh Chatterjee
NEUROSCIENCE INSIGHTS
(2020)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
