Article
Chemistry, Organic
Sundaram Maurya, Sandip B. Jadhav, Rambabu Chegondi
Summary: An efficient and mild transition-metal free formal C(sp(2))-H arylation method is reported, which does not require pre-functionalization and is environmentally friendly with high yield.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Tamanna, Yaseen Hussain, Deepak Sharma, Pankaj Chauhan
Summary: A highly functionalized isochroman was synthesized with high enantio- and diastereoselectivity through an organocatalyzed domino reaction. Quinidine catalyzed the peroxyhemiacetalization/oxa-Michael/desymmetrization domino sequence between 2,5-cyclohexadienone-tethered aryl aldehydes and hydroperoxides, resulting in isochromans with a cyclohexenone ring and three vicinal stereocenters in good yields and high enantioselectivities under ambient reaction conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Xu Gong, Juan Huang, Xiangrui Sun, Ziling Chen, Ming Yang
Summary: Illicium sesquiterpenes, a family of biologically active secondary metabolites, have been synthesized using a comprehensive biosynthetic pathway and a synthetic route to illisimonin A and merrilactone A.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Qiuyu Li, Rui Pan, Meihui Wang, Hequan Yao, Aijun Lin
Summary: In this study, ligand-controlled, palladium-catalyzed asymmetric [4+4] and [2+4] cycloaddition reactions of benzofuran-derived azadienes were developed. Different chiral ligands were utilized to synthesize various cyclic compounds with high enantioselectivity.
Article
Chemistry, Multidisciplinary
Vaibhav B. Patil, Jagadeesh Babu Nanubolu, Rambabu Chegondi
Summary: A one-pot sequential reaction has been designed for the efficient construction of tetrahydrofuran containing spiro-cyclohexadienones, involving p-hydroxybenzylation, oxidative dearomatization, and spiroannulation. Additionally, Friedel-Crafts alkylation of spiro[4.5]cyclohexadienones with indoles provides a wide array of highly diastereoselective products, depending on the ring size of the fused cyclic ketones.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Naveen Diddi, Dale E. Ward
Summary: The total synthesis of dolabriferol C was achieved by a series of unique chemical reactions, simplifying the synthetic process significantly. This synthetic approach combines different stereochemical selectivities and enantioselective reactions, providing new insights for the study of related compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Engineering, Environmental
Xu Gong, Chen-Han Lu, Wei-Kai Lee, Pan Li, Yu-Hsin Huang, Zhanxiang Chen, Lisi Zhan, Chung-Chih Wu, Shaolong Gong, Chuluo Yang
Summary: By designing rigid and strong electron-rich donor moieties, researchers synthesized two red emitters with high rigidity and linear D-A molecular skeleton, showing distinct TADF nature and high efficiencies. The resulting OLEDs achieved high external quantum efficiency and excellent emission characteristics in the red color gamut.
CHEMICAL ENGINEERING JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Mohamed S. H. Salem, Shinobu Takizawa
Summary: Anionic salicylimine-based cobalt (III) complexes with chiral ligands derived from isoleucine amino acids were used as efficient bifunctional phase-transfer catalysts for electrophilic iodination and intermolecular iodoacetalization of enol ethers, achieving high yields and enantioselectivities.
FRONTIERS IN CHEMISTRY
(2022)
Article
Chemistry, Organic
Shubham Debnath, A. Sanjeeva Kumar, Sachin Chauhan, K. C. Kumara Swamy
Summary: The reactivity of 2-sulfonamidoindoles with acetoxy allenoates under phosphine catalysis is dependent on the position of the acetoxy (OAc) group on the allenoate. The reaction can lead to different annulation products depending on the temperature-controlled conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Wei Ju, Xudong Wang, Hailong Tian, Jinghan Gui
Summary: The first total synthesis of polychlorinated steroids clionastatins A and B was accomplished by means of a convergent, radical fragment coupling approach. Key features of the synthesis include an Ireland-Claisen rearrangement, regioselective acyl radical conjugate addition, intramolecular Heck reaction, and diastereoselective olefin dichlorination. This work also led to the determination that the true structures of clionastatins A and B are C14 epimers of the originally proposed structures.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Vitor A. Fernandes, Rafaely N. Lima, Yoisel B. Broterson, Meire Y. Kawamura, Radell Echemendia, Alexander F. de la Torre, Marco A. B. Ferreira, Daniel G. Rivera, Marcio W. Paixao
Summary: An efficient strategy combining stereocontrol of organocatalysis with diversity-generating character of multicomponent reactions was used to produce structurally unique, tetrasubstituted cyclopentenyl frameworks. This approach yielded a diversity of structurally complex compounds with high stereoselectivity and moderate to high yields, including peptidomimetics and natural product hybrids.
Review
Chemistry, Organic
Suven Das
Summary: This review highlights novel stereoselective strategies for the synthesis of various heterocycles using isoquinolinium salts. These reactions offer advantages such as high stereoselectivity, readily available starting materials, and mild reaction conditions, and have been successfully used in the synthesis of natural products and bioactive compounds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Zhimin Xing, Bowen Fang, Shangwen Luo, Xingang Xie, Xiaolei Wang
Summary: Seven-membered polycyclic architectures, commonly found in natural products and molecular drugs, are challenging targets in synthesis. This study presents a base-induced ring expansion as a general strategy for constructing a wide range of fused seven-membered ring systems. The successful synthesis of two sesquiterpenoids, plecarpenene and plecarpenone, demonstrates the efficacy of this method for constructing fused bicyclo[5.3.0]decane skeletons.
Article
Chemistry, Multidisciplinary
Hong-Cheng Shen, Ying Chen, Ying Zhang, He-Ming Jiang, Wen-Qian Zhang, Wen-Ao Li, Mostafa Sayed, Xinhao Zhang, Yun-Dong Wu, Liu-Zhu Gong
Summary: The study demonstrates a nickel-catalyzed enantioselective desymmetrizing aza-Heck cyclization, utilizing a pentafluorobenzoyl leaving group and chiral pybox ligand, with a competitive E2-like pathway and beta-H elimination at the enantioselectivity determining step.
Article
Chemistry, Organic
Pallabita Basu, Nishikant Satam, Soumyaranjan Pati, Alati Suresh, Irishi N. N. Namboothiri
Summary: The reactivity of Hauser-Kraus (H-K) donor, 3-sulfonylphthalide, with various activated imines under basic conditions is demonstrated. Depending upon the stoichiometry of the base, the reaction of 3-sulfonylphthalide with Boc-protected aldimine provides access to 1,2-imine adducts and alkylidenephthalides. The alkylidenephthalides can be transformed to ketophthalides, and Boc-protected isatinimines can undergo efficient H-K annulation to provide spiro-isoquinolinone-oxindoles.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Aamer Saeed, Atteeque Ahmed, Pervaiz Ali Channar, Ghulam Shabir, Abbas Hassan, Zia-ur-Rehman, Qamar Abbas, Mubashir Hassan, Hussain Raza, Sung-Yum Seo, Hesham R. El-Seedi
Summary: Tyrosinase is a multi-copper enzyme that plays a critical role in melanogenesis and browning process important to cosmetics and food industries. A series of symmetrical Bis-Azo-Azamethine hybrids were synthesized and compound 5i was found to be the most potent inhibitor with strong free radical scavenging activity, suggesting its potential applications in inhibiting melanogenesis and oxidative stress.
JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS
(2022)
Article
Chemistry, Medicinal
Michele Panciera, Emilio Lence, Angela Rodriguez, Begona A. Gracia, Jose Ainsa, Clara Marco-Marin, Vicente Rubio, Carlos Roque Duarte Correia, Concepcion Gonzalez-Bello
Summary: The therapeutic potential of 3H-pyrrolo[2,3-c]quinolines, the main core of Marinoquinoline natural products, has been explored for the development of new anti-TB agents. Two pyrroloquinolines (compounds 50 and 54) were discovered to have good in vitro activity against virulent strains of Mycobacterium tuberculosis. Enzymatic assays revealed that both compounds are inhibitors of glutamate-5-kinase (G5K), an essential enzyme for this pathogen.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Pervaiz Ali Channar, Mubashir Aziz, Syeda Abida Ejaz, Gul-e-Saba Chaudhry, Amna Saeed, Rabail Ujan, Abbas Hasan, Syeda Rabia Ejaz, Aamer Saeed
Summary: The synthesis of compounds with a thiazolidinone pharmacophore was achieved, and their anticancer activities were evaluated. Compounds 2c and 2d exhibited significant cytotoxicity against MCF-7 and HeLa cell lines by inducing apoptosis. Molecular docking and dynamic simulations provided further support to these findings, and computational studies suggested the potential of these compounds as lead molecules for the development of novel drug candidates for specific cancers.
JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS
(2023)
Review
Chemistry, Organic
Ahsanullah, Abbas Hassan, Farzana L. Ansari, Joerg Rademann
Summary: The modification of native peptides to peptidomimetics is an important goal in medicinal chemistry, and using Meldrum's acid and phosphorus and sulfur ylides for peptide-compatible C-acylation is an effective method to achieve this goal.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Haseen Ahmad, Waqar Ahmed, Abbas Hassan
Summary: Copper-mediated transformation enables the successful C-N coupling of thiazole appendant aryl halides with various amides, leading to the formation of amide products with high yields.
Review
Chemistry, Medicinal
Abbas Hassan, Abid Hussain Khan, Faiza Saleem, Haseen Ahmad, Khalid Mohammed Khan
Summary: This review provides a comprehensive overview of the biological applications of oxadiazole-containing drugs from 2013 to 2021. Oxadiazoles have shown wide range of medicinal properties and have been widely used in medicinal chemistry, agriculture, and neuroprotection. The unique features of the oxadiazole scaffold make it a significant pharmacophore.
EXPERT OPINION ON THERAPEUTIC PATENTS
(2022)
Article
Chemistry, Organic
Rifhat Bibi, Ismat Ullah Khan, Abbas Hassan
Summary: A structure selectivity relationship was established by modifying the ligand structure, which greatly influenced the catalytic activity and selectivity of the catalyst for non-activated substrates in the Heck-Matsuda reaction. The ligand 6MesPyoxsBu showed optimal catalytic activity and selectivity.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Applied
Tomaz Henrique Duarte Chorro, Edson Leonardo Scarpa de Souza, Otto Daolio Koster, Ellen Christine Polo, Rafaela Costa Carmona, Vitor Hugo Menezes da Silva, Joao Marcos Batista Junior, Carlos Roque Duarte Correia
Summary: A new enantioselective intramolecular strategy for the synthesis of enantioenriched bridged benzoxacines, unsaturated spirobenzofurans, 2,3-dihydrobenzofuran, and 2,3-indoline acetate scaffolds directly from anilines has been developed. The process combines in situ diazotization of the aniline with intramolecular Heck-Matsuda reaction, eliminating the need for isolation and purification of potentially unstable or hard-to-synthesize aryldiazonium salts. The method has been demonstrated to be practical and robust, achieving high yields and enantiomeric ratios.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Biochemistry & Molecular Biology
Zahra Begum, Saif Ullah, Muhammad Akram, Muhammad Uzair, Farman Ullah, Ahsanullah, Julie Pelletier, Jean Sevigny, Jamshed Iqbal, Abbas Hassan
Summary: A series of thienopyrimidines were synthesized and screened for their inhibitory activity against h-NTPDases. Molecular docking study revealed the interactions between these compounds and important amino acid residues of the respective h-NTPDase isozymes.
BIOORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Carson Wiethan, Ingredy B. Braga, Vitor H. Menezes da Silva, Joao M. Batista Jr, Carlos Roque D. Correia
Summary: The enantioselective synthesis of isoindolones via Heck-Mizoroki reactions of endocyclic enamides using a palladium-bis(oxazoline) catalyst system is described. N,N-ligands prove to be an effective and low-cost alternative to phosphine-based chiral ligand counterparts. The intramolecular Heck reaction enables the construction of tricyclic isoindolones containing chiral centers in high yields and enantiomeric ratios.
Article
Chemistry, Medicinal
Gohar Zaman, Saif Ullah, Muhammad Uzair, Sania Batool, Haseen Ahmad, Farman Ullah, Julia Pelletier, Jean Sevigny, Jamshed Iqbal, Abbas Hassan
Summary: In this study, various thieno[3,2-d]pyrimidine derivatives were synthesized by treating different secondary amines through aromatic nucleophilic substitution reaction (SNAr) followed by Suzuki reaction. The synthesized compounds were screened for their hydrolytic activity inhibition against h-NTPdase1, h-NTPdase2, h-NTPdase3, and h-NTPdase8. Compound N-benzyl-N-methyl-7-phenylthieno[3,2-d]pyrimidin-4-amine 3j selectively inhibited h-NTPdase1 activity with an IC50 value of 0.62 +/- 0.02 µM, while compound 4d was the most potent inhibitor of h-NTPdase2 with a sub-micromolar IC50 value of 0.33 +/- 0.09 µM. Similarly, compounds 4c and 3b were found to be selective inhibitors for isozymes h-NTPdase3 (IC50=0.13 +/- 0.06 µM) and h-NTPdase8 (IC50=0.32 +/- 0.10 µM), respectively. Molecular docking study revealed the interactions with important amino acid residues.
Article
Chemistry, Organic
Valdeir C. de Oliveira, Ricardo A. Angnes, Joao M. Batista Jr, Carlos Roque D. Correia
Summary: This work presents an effective method for the synthesis of chiral vinyl cyclopentenols via Heck desymmetrization of cyclopent-3-en-1-ylmethanol using vinyl triflates as coupling agents and chiral N,N ligands. The reaction exhibited high enantioselectivity and diastereoselectivity, with isolated yields of up to 80% and enantiomeric ratios of up to 97:3. The diastereoselectivities were rationalized through experiments using different vinyl triflates and the desymmetrization of a protected olefin substrate.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Engineering, Environmental
Edson Leonardo Scarpa de Souza, Tomaz Henrique Duarte Chorro, Carlos Roque Duarte Correia
Summary: Arenediazonium salts are important aromatic organic compounds used as building blocks in academia and industry. Tetrafluoroborate arenediazonium salts are generally stable at room temperature, but those containing heteroatoms in the aromatic moiety can be problematic and unstable. This study evaluated the thermal stability and potential hazards of 58 common arenediazonium tetrafluoroborate salts, providing guidance for their safe use and handling in organic synthesis.
PROCESS SAFETY AND ENVIRONMENTAL PROTECTION
(2023)
Article
Chemistry, Organic
A. A. Strekalova, A. A. Shesterkina, E. Shuvalova, C. R. D. Correia, Boqing Xu, Xuezhi Duan, Yanhui Yang, L. M. Kustov
Summary: The catalytic synthesis of isoprenol by hydrogenation of 3-methylbut-3-en-1-yl acetate on heterogeneous bimetallic Cu-Pt catalysts was successfully carried out for the first time. The best selectivity of isoprenol (76%) and full ester conversion were achieved using the 5%Cu-1%Pt/SiO2 catalyst within 6 hours.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
A. Murashkina, A. D. Averin, S. P. Panchenko, A. S. Abel, O. A. Maloshitskaya, E. N. Savelyev, B. S. Orlinson, I. A. Novakov, C. R. D. Correia, I. P. Beletskaya
Summary: In this study, the N-arylation of n-octylamine and adamantane-containing amines with iodobenzene and its derivatives was achieved using copper(I) iodide and copper nanoparticles as catalysts in DMSO. Various ligands were used, and it was found that 2-isobutyrylcyclohexanone was the most efficient ligand. Higher yields of arylation products were obtained in the presence of copper nanoparticles, which could be recycled up to 9 times without significant loss of yield.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
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)
