Article
Chemistry, Organic
Shuyu Meng, Yinglan Wang, Jie Liu, Jie Zheng, Xiao Qian, Quanrui Wang
Summary: In the presence of boron trifluoride, alkynyl sulfides and alkynyl sulfoxides undergo tandem cross-coupling and [3,3]-sulfonium rearrangement, followed by 5-exo-dig heterocyclization to produce novel tetrasubstituted furans. The method shows good efficiency and 100% atom-economy, allowing further derivatization of the resulting furans.
Article
Biochemistry & Molecular Biology
Mingliang Zhang, Pin Zhao, Qilv Liu, Xinlei Liu, Jingya Hu, Dongqing Wu, Lantao Liu
Summary: A catalyst-free tandem reaction for the construction of C(sp(3))-O bonds through aza-Michael addition and C(sp(3))-O bond formation was developed. Substituted amino ferrocenes reacted with quinone esters to produce N-ferrocene-substituted benzodihydrooxazoles in moderate to excellent yields (up to >99% yield). The quinone esters acted as both substrate and oxidant in this transformation. Key features of this method include good functional group tolerance, broad substrate scope, and mild reaction conditions.
Article
Chemistry, Organic
Sana Jamshaid, Yong Rok Lee
Summary: A novel, facile, and efficient Lewis-acid-catalyzed [4 + 1] annulation protocol has been developed for the construction of functionalized polycyclic-fused furans. This methodology provides a rapid synthetic route to divergently orientated polycyclic furans in good yields, without the need for transition metals and ligands. Additionally, this protocol can be used to synthesize multisubstituted furans.
Correction
Chemistry, Organic
Mu-Xue He, Yan Yao, Chun-Zhi Ai, Zu-Yu Mo, Yu-Zheng Wu, Qi Zhou, Ying-Ming Pan, Hai-Tao Tang
Summary: This paper examines the electrochemically-mediated C-H functionalization method for constructing tetrasubstituted furan compounds.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Hari K. Akula, Suyeal Bae, Padmanava Pradhan, Lijia Yang, Barbara Zajc, Mahesh K. Lakshman
Summary: The underexploited potential of N-unprotected 8-formyl derivatives of adenosine and 2'-deoxyadenosine for C8 modifications of these nucleosides is discussed in this study. The researchers report the straightforward and scalable synthesis of N-unprotected 8-formyladenine nucleoside derivatives, and demonstrate their versatility for C8 diversification through various reactions.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Song Li, Haibei Li, Chen-Ho Tung, Lei Liu
Summary: This study reports a bio-inspired nonheme-iron-catalyzed method for the efficient and selective preparation of diversely functionalized organosilanols. The practical method allows for the synthesis of organosilanols with different substituent patterns and exhibits good functional group tolerance. The study also demonstrates the potential application of this method in the synthesis of functional molecules containing silanols.
Review
Biochemistry & Molecular Biology
Alejandro Torregrosa-Chinillach, Rafael Chinchilla
Summary: This review summarizes the recent advances in oxidative dehydrogenation of C-N and C-O bonds, leading to C=N and C=O bonds, respectively, using air or pure oxygen as oxidants and metal-free homogeneous or recyclable heterogeneous photocatalysts under visible light irradiation.
Article
Biochemistry & Molecular Biology
Neetu Yadav, Mohd Danish Ansari, Vijay B. Yadav, Ankit Verma, Saurabh K. Tiwari, Saif Ansari, I. R. Siddiqui
Summary: A visible-light-mediated, one-pot three-component reaction using organophotoredox catalyst Eosin Y in EtOH:H2O was developed for the synthesis of 3-functionalized indole derivatives. The green light source used is inexpensive and sustainable, making the protocol compatible with green chemistry demands.
MOLECULAR DIVERSITY
(2021)
Article
Biochemistry & Molecular Biology
Claudia Feberero, Cintia Virumbrales, Carlos Sedano, Lorena Renedo, Samuel Suarez-Pantiga, Roberto Sanz
Summary: A straightforward and transition metal-free one-pot protocol for synthesizing halobenzo[b]furans has been developed using easily available starting materials. The researchers fine-tuned the different steps involved to achieve a successful one-pot procedure and synthesized a wide variety of new halobenzo[b]furans.
Review
Chemistry, Multidisciplinary
Anogh Ghosh, Pranjal Pyne, Sumit Ghosh, Debashis Ghosh, Souvik Majumder, Alakananda Hajra
Summary: This article presents a metal-free photoinduced methodology for cross-coupling between different C(sp(3))-H sources and heteroarenes to construct Csp(2)-Csp(3) bonds. This method utilizes organic photosensitizers and light as a clean energy source, making it efficient and environmentally friendly, suitable for applications in the chemical and pharmaceutical industries.
Review
Chemistry, Organic
Rodrigo Abonia, Oscar Montoya
Summary: This review examines the progress in literature on the synthesis of 1,2,2-triarylethanone derivatives from 2000 to 2020, exploring various synthetic approaches such as metal-free, metal-mediated, C-H bond activation, alpha-monoarylation, alpha,alpha-diarylation, umpolung processes, N heterocyclic carbene (NHC), and deoxygenation. Mechanistic proposals and reported data on carbon-carbon bond formation through ketone based alpha-arylation processes are also briefly discussed and organized for comparison in concise Tables/Schemes.
CURRENT ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Yaxuan Jing, Mohsen Shakouri, Xiaohui Liu, Yongfeng Hu, Yong Guo, Yanqin Wang
Summary: Researchers have developed a strategy to selectively cleave C-C bonds in aromatic plastics using catalyst Ru/Nb2O5 through methanol poisoning, resulting in monocyclic phenolic compounds.
Article
Chemistry, Organic
Yanhui Wang, Yihan Tang, Yuwei Zong, Gavin Chit Tsui
Summary: We describe a method for the selective C-F bond functionalization of tetrasubstituted gem-difluoroalkenes and trisubstituted monofluoroalkenes using Grignard reagents without the transition metal catalyst.
Article
Chemistry, Inorganic & Nuclear
Harish S. Kunchur, Maravanji S. Balakrishna
Summary: The reactions of amide functionalized bisphosphine with platinum salts were studied, resulting in the formation of various complexes. The mechanism of the formation of 1,2-azaphospholene was investigated. Additionally, a palladium complex with low catalyst loading showed excellent catalytic activity in the N-alkylation reaction of amines with alcohols.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Shubham Sharma, Dharmender Singh, Sunit Kumar, Vaishali, Rahul Jamra, Naveen Banyal, Deepika, Chandi C. Malakar, Virender Singh
Summary: An operationally simple and metal-free approach is described for the synthesis of pyrazole-tethered thioamide and amide conjugates. The advantages of this developed protocol refer to the broad substrate scope, metal-free and easy to perform reaction conditions. Moreover, the pyrazole C-3/5-linked amide conjugates were also synthesized via an oxidative amination of pyrazole carbaldehydes and 2-aminopyridines using hydrogen peroxide as an oxidant.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Kishore Kumar Palli, Palash Ghosh, Shiva Krishna Avula, B. Sridhara Shanmukha Rao, Amol D. Patil, Subhash Ghosh, Gangarajula Sudhakar, Chada Raji Reddy, Prathama S. Mainkar, Srivari Chandrasekhar
Summary: Remdesivir, the first drug approved by the FDA to treat COVID-19, is highly demanded for patients infected with the SARS-CoV-2 virus. A facile approach minimizing protecting group manipulations to afford remdesivir in good overall yield is reported in this study.
TETRAHEDRON LETTERS
(2022)
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
Chemistry, Organic
Chada Raji Reddy, Siddique Z. Mohammed, Paridala Kumaraswamy, Roshan Chandrakant Kajare, Amol D. Patil, V. S. Rao Ganga, Andhavaram Ramaraju, Balasubramanian Sridhar
Summary: An effective synthetic approach for the construction of diverse bicyclic fused cyclopentenones from Morita-Baylis-Hillman (MBH) carbonates of propiolaldehydes has been demonstrated. The transformation involves the propargylation of an alkenylamine with an MBH carbonate followed by the Pauson-Khand reaction to yield cyclopentenone fused with aza-cycles having additional functionality.
SYNTHESIS-STUTTGART
(2022)
Article
Biochemistry & Molecular Biology
Nicolas Levoin, Appala Venkata Ramana Murthy, Vennu Narendar, Nangunoori Sampath Kumar, Pasula Aparna, Anagani Kanaka Durga Bhavani, Chada Raji Reddy, Paul Mosset, Rene Gree
Summary: A series of compounds with piperidine-triazole scaffolds were found to have strong affinity for dopamine and sigma receptors, with selectivity towards specific receptors and channels. The lead compound showed agonist activity and suggested the presence of a calcium-binding regulatory site.
BIOORGANIC & MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Organic
Chada Raji Reddy, Veeramalla Ganesh, Nagender Punna
Summary: Unprecedented domino aza-annulations of (E)-2-en-4-ynyl-acetonitriles with sodium azide under metal-and oxidant-free conditions for the assembly of triazolo-pyridines are accomplished. The developed strategy offers broad substrate scope and demonstrated its synthetic utility via denitrogenative coupling of fused triazoles with different nucleophiles.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Dabbugoddu Brahmaiah, Anagani Kanaka Durga Bhavani, Pasula Aparna, Nangunoori Sampath Kumar, Helene Solhi, Remy Le Guevel, Blandine Baratte, Thomas Robert, Sandrine Ruchaud, Stephane Bach, Surender Singh Jadav, Chada Raji Reddy, Paul Mosset, Nicolas Gouault, Nicolas Levoin, Rene Gree
Summary: Three series of CLK1 inhibitors were designed, synthesized, and tested against CLKs and DYRK1A kinases. A promising derivative 12g was discovered, showing significant inhibition activity against HsCLK1 and HsDYRK1A. Molecular modeling and kinome scan analysis further supported these results, suggesting the potential for developing selective inhibitors in this kinase family.
Article
Chemistry, Multidisciplinary
Chada Raji Reddy, Muppidi Subbarao, Dattahari H. Kolgave, Uprety Ajaykumar, Puthiya Purayil Vinaya
Summary: An efficient and straightforward method for the synthesis of diversified seleno-azaspiro-2,5-cyclohexadienones from N-(4-methoxy aryl)propiolamides using elemental selenium and boronic acids has been demonstrated. This method can also be extended to N-(4-methoxy aryl)propiolates and biaryl ynones to access the corresponding selenylated oxospiro-2,5-cyclohexadienones and spiro[5,5]trienones, respectively.
Article
Chemistry, Organic
Chada Raji Reddy, Karna Nair, Amol D. Patil, Ramachandra Reddy Donthiri, Rene Gree
Summary: A novel one-pot base-promoted insertion reaction of indolyl 2-alkynes into a C-C single bond of 1,3-diketones, followed by intramolecular aldol reaction and dehydrative aromatization, has been described. This reaction cascade allows for the construction of 2-indolyl phenols, involving the formation of both C1-C2 and C3-C4 bonds of phenols with a good substrate range. Furthermore, these bifunctional compounds can be used in a novel arylative annulation in the presence of Grignard reagents to provide chromeno-indole frameworks.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Applied
Chada Raji Reddy, Muppidi Subbarao, Anjali Rathaur, Ejjirotu Srinivasu
Summary: This paper reports the Rh(III)-catalyzed cascade oxidative C-H functionalization/aza-annulation of indole and pyrrole-N-carboxamides with 1,3-enynes involving 1,4-rhodium migration. It provides an approach for the synthesis of imidazo[1,5-a]indol-3(2H)-ones from easily accessible substrates. The compatibility of sulfonamides in this method is also demonstrated, leading to the corresponding benzo[d]sultams.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Chada Raji Reddy, Uprety Ajaykumar, Dattahari H. Kolgave, Remya Ramesh
Summary: A variety of unactivated N-benzyl acrylamides underwent dearomative ipso-cyclization induced by sulfur-centered radicals in the presence of ceric ammonium nitrate as the oxidant to produce azaspirocycles in good yields. This represents the first report on ipso-dearomatization of N-benzyl acrylamides without substituents at the para-position of the aromatic ring. The reaction conditions are also applicable to substrates with substituents at the para-position such as F, NO2, OMe, OH, and OAc.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Chada Raji Reddy, Ankita Kumari, Suraj Aswale, Amol D. Patil, Y. Lakshmi Prapurna
Summary: The reaction of alkynyl p-quinone methide (pQM) with keto-methylenes through a base-mediated tandem 1,6-addition/annulation sequence, [2 + 3] annulation, affords furans for the first time. Various functionalized furans, including fused derivatives, can be obtained in good to excellent yields under mild reaction conditions. The effectiveness of alkynyl pQMs is demonstrated by their ability to access isoxazoles, pyrazoles via [3 + 2] annulation, and pyridines through [3 + 3] annulation in the presence of different bis-nucleophiles.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Chada Raji Reddy, Uprety Ajaykumar, Amol D. Patil, Remya Ramesh
Summary: A CAN-promoted oxidative ipso-cyclization of unactivated biaryl ynones with S-centered radicals has been developed for the synthesis of spiro[5,5]trienones. The method exhibited excellent regioselectivity towards spirocyclization and tolerated various functional groups. Dearomatization of previously unknown aryl/heteroaryl groups was also achieved. DMSO was employed as a low-toxicity, inexpensive solvent and oxygen source.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Chada Raji Reddy, Veeramalla Ganesh, Nagender Punna
Summary: This article describes a base-mediated unexpected aminative carbo-cyclization of cyano-enynyl esters, generated from Morita-Baylis-Hillman (MBH) acetates of propiolaldehydes, with secondary-amines. This metal-free reaction allows the synthesis of a unique cyclopentenone bearing an exocyclic double bond (cyano-olefin) with high E-selectivity in good yields. The synthetic potential of this annulation was further exemplified by the derivatization of bioactive molecules, a scale-up synthesis and synthetic transformations of the obtained cyclopentenone.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Chada Raji Reddy, Dattahari H. Kolgave, Uprety Ajaykumar, Remya Ramesh
Summary: A copper-catalyzed ipso-annulation reaction of N-(p-methoxyaryl)propiolamides with 1,3-diketones has been developed, enabling the synthesis of diketoalkylated spiro[4.5]trienones and spiro[5.5]trienones.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Chada Raji Reddy, Mayur C. Bhandari, Amol D. Patil, Mounika Aila, Ramachandra Reddy Donthiri
Summary: An efficient selenylative cyclization of aryl-alkynones with diselenides in the presence of iron(iii)chloride at room temperature to prepare 3-seleno-2-naphthols in good yields has been described. Furthermore, the resulting products were transformed into selenyl-naphthofuran and selenyl-1,2-naphthoquinone derivatives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)