Article
Chemistry, Organic
Naoto Sugisawa, Kohei Nakabayashi, Hiroki Sugisawa, Shinichiro Fuse
Summary: We have developed one-step syntheses for unsymmetrical sulfamides and N-substituted sulfamate esters by modifying the nucleophile and tertiary amine. Symmetrical sulfite formation was prevented by changing the tertiary amine during the synthesis of N-substituted sulfamate esters. The impact of tertiary amines was explained using linear regression. Our approach allows for rapid production (<= 90 s) of desired products with labile acidic and/or basic groups under mild (20 degrees C) conditions, eliminating the need for tedious purification.
Article
Chemistry, Organic
Yuta Kondo, Hiroyuki Morimoto, Takashi Ohshima
Summary: In this article, we summarize our recent efforts in developing catalytic methods for synthesizing N-unsubstituted ketimines and their applications in one-pot reactions for producing various nitrogen-containing compounds. The account provides detailed background, optimization, scope, and mechanistic information. We hope that this work will stimulate further studies on the implementation of N-unsubstituted ketimines.
Article
Chemistry, Organic
Iwao Hachiya, Kenta Nakamura, Masaya Hara, Koki Sato, Makoto Shimizu
Summary: The domino 1,4- and 1,4-addition reactions of ketene silyl thioacetals to dialkynyl imines were revealed in this study, with scandium triflate acting as a catalyst to yield a variety of alkynyl delta-lactams in moderate to good yields.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Luiz S. Longo, Fernanda A. Siqueira, Nicolas S. Anjos, Gabriela F. D. Santos
Summary: This review summarizes the recent progress on the use of scandium(III) triflate as a Lewis acid catalyst for multicomponent reactions in the synthesis of nitrogen-containing heterocycles, which are valuable privileged scaffolds in Organic and Medicinal Chemistry.
Article
Chemistry, Organic
Baofu Zhu, Jiaming He, Kai Zou, Anquan Li, Chen Zhang, Jiaji Zhao, Hua Cao
Summary: This study established a three-component reaction catalyzed by base, involving ynals, isocyanates, amines, and alcohols. The strategy enables a wide range of substrates and provides a simple process for the preparation of diverse pyridine derivatives with good yields and high regioselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Meng-Yang Chang, Chun-Yi Lin
Summary: In this study, a one-pot construction method for diversified sulfonyl flavones was developed. The alpha-sulfonyl o-hydroxyacetophenones were reacted with substituted nitriles through a K2CO3-mediated (5+1) stepwise annulation under open-flask atmosphere conditions. This method offers intermolecular and intramolecular ring-closure pathways by forming a carbon-oxygen single bond, a carbon-carbon double bond, and cleaving a carbon-nitrile triple bond.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Louis G. Mueller Jr, Taylor M. Keller, Fraser F. Fleming
Summary: Substituted oxazoles and imidazoles can be synthesized in one pot using the isocyanide building block Asmic, an alkyl halide, and an acid chloride or nitrile. The modular assembly involves sequential deprotonation-alkylation and deprotonation-acylation or imination of Asmic, followed by a unique carbon-sulfur bond cleavage to construct the azole. This strategy is robust, highly efficient, and allows for the formation of C4-C5 disubstituted oxazoles or imidazoles in a single operation.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Fei Ma, Jie Li, Shuning Zhang, Yuang Gu, Tingting Tan, Wanting Chen, Shuyue Wang, Hongtao Xu, Guang Yang, Richard A. Lerner
Summary: Metal-catalyzed one-pot reaction using DNA encoding has been developed for the formation of C(sp(2))-C(sp(3)) and C(sp(3))-S bonds. The reaction shows wide substrate scopes and moderate to excellent yields, greatly expanding the chemical space of DNA-compatible reactions and the molecular scaffold diversity of DNA-encoded libraries.
Article
Chemistry, Physical
Hailong Zhang, Romain Carlino, Regis Guillot, Richard Gil, Sophie Bezzenine, Jerome Hannedouche
Summary: A new method for efficient cyclization of δ/ε-alkenoic acids and N-protected δ-alkenamides using easily accessible Lewis acid scandium(III) triflate under thermal and microwave conditions is reported for the first time. The selectivity of the reaction depends on the substitution patterns of the backbone chain and alkene moiety, resulting in exclusive formation of γ/ε-lactones via O-selective cyclization or Friedel-Crafts-type products via C-selective cyclization. Uncommon O-selective cyclization occurred preferentially or exclusively with N-protected δ-alkenamides, confirmed by single crystal X-ray crystallography.
Article
Chemistry, Organic
Wei Wu, Beibei Luo, Yi You, Zhiqiang Weng
Summary: A novel synthesis approach for the construction of 2-trifluoroethyl-substituted benzofurans under copper-catalyzed conditions has been developed, with moderate to excellent yields (up to 93%). This method is also applicable to the formation of 2-trifluoroethylated indoles.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Santosh D. Jadhav, Tavinder Singh, Naveen Thakur, Anand Singh
Summary: A straightforward and efficient Ag(I) catalyzed domino reaction has been reported for the synthesis of unsymmetrical diarylacetate and triarylmethane derivatives. This strategy is versatile and provides excellent yields.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Maki Minakawa, Keisuke Minami, Yuya Sato
Summary: A simple and environmentally friendly method for preparing S-heterocycles using aromatic thiols and diols in cyclization reactions with H2O as a byproduct was described. The Sc(OTf)(3)-catalyzed dehydrative cyclizations of aromatic thiols and diols allowed for the synthesis of thiopyran and thiophene derivatives, with control experiments providing insights into the reaction pathway.
Article
Chemistry, Multidisciplinary
Cunyuan Zhao, Yuankai Wang, Quan Pham, Changhang Dai, Abhishek Chatterjee, Masayuki Wasa
Summary: We present a practical catalytic method to modify bioactive amide-based natural products and other small-molecule drugs with different functional handles in order to synthesize drug conjugates. By using a combination of readily available Sc-based Lewis acids and N-based Bronsted bases, we demonstrate the ability to deprotonate amide N-H bonds in multifunctional drug molecules. The resulting amidate can undergo an aza-Michael reaction with α,β-unsaturated compounds, leading to drug analogues with alkyne, azide, maleimide, tetrazine, or diazirine moieties under mild conditions. We showcase the utility of this chemical tagging strategy by producing drug conjugates through click reactions between alkyne-tagged drug derivatives and an azide-containing green fluorescent protein, nanobody, or antibody.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Tanawat Phumjan, Poramate Songthammawat, Jira Jongcharoenkamol, Paratchata Batsomboon, Somsak Ruchirawat, Poonsakdi Ploypradith
Summary: Starting from benzaldehyde derivatives, 9-anthraldehydes were prepared in good yields through a series of steps involving epoxidation and acid-catalyzed processes. Factors affecting the yield included the nature of the alcohol substrate and substituents on the aromatic ring. Mechanistic studies revealed that the semipinacol rearrangement of the epoxide is a crucial step in the formation of 9-anthraldehydes.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jiayue Fu, Bingbing Li, Xinxiu Wang, He Wang, Minghui Deng, Huali Yang, Bin Lin, Maosheng Cheng, Lu Yang, Yongxiang Liu
Summary: Benzo[c]phenanthridine alkaloids, belonging to the isoquinoline alkaloids family, are extracted from rutaceae, papaveraceae, and other plants in the middle and lower basins of the Yangtze River. More than 100 alkaloids have been isolated since the first discovery in 1839, with representative structures shown in Scheme 1.
Article
Chemistry, Medicinal
Muthuraj Prakash, Yukihiro Itoh, Yoshie Fujiwara, Yukari Takahashi, Yuri Takada, Paolo Mellini, Elghareeb E. Elboray, Mitsuhiro Terao, Yasunobu Yamashita, Chika Yamamoto, Takao Yamaguchi, Masayuki Kotoku, Yuki Kitao, Ritesh Singh, Rohini Roy, Satoshi Obika, Makoto Oba, Dan Ohtan Wang, Takayoshi Suzuki
Summary: This study aimed to design novel FTO-selective inhibitors by merging fragments of previously reported FTO inhibitors, resulting in compound 11b selectively inhibiting FTO. Treatment with a prodrug of 11b decreased the viability of acute monocytic leukemia cells, altered the level of the FTO substrate N-6-methyladenosine in mRNA, and induced changes in expression of FTO target genes MYC and RARA.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Anirban Mukherjee, Ritesh Singh, Kishor D. Mane, Gourab Kanti Das
Summary: Pure quantum mechanical calculations were used to determine the regioselectivity under metalloradical catalysis by Co(II)-porphyrin. The study found that regioselectivity is inherent to the aminyl radical generated from the sulfamoyl azide substrate. Different conformations for the transition state were analyzed to find the most stable conformation for preferable selectivity, in agreement with experimental results.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Deblina Roy, Grace Kaul, Abdul Akhir, Ashok Kumar Sharma, Satyen Saha, Sidharth Chopra, Gautam Panda
Summary: A library of diarylmethyl amines targeting ESKAPE bacterial pathogens was synthesized, and compounds with potent antibacterial activity against Gram-positive bacteria were identified. The presence of lipophilic and nitrogenous components was found to be important for antibacterial activity.
Article
Chemistry, Organic
Amit Kumar, Gaurav Sharma, Sanjeev K. Shukla, Gautam Panda
Summary: A tandem reaction involving semipinacol rearrangement and aldehyde arylation or alkylation has been discovered. This reaction allows for the formation of functionalized 1,3-diols bearing three consecutive tertiary stereocenters from various trisubstituted 2,3-epoxy alcohols and Grignard reagents. The resulting 1,3-diols are confirmed to exist in the anti configuration.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Amit Kumar, Neetu Kumari, Sandeep Bhattacherjee, Umamageswaran Venugopal, Shahid Parwez, Mohammad Imran Siddiqi, Manju Y. Krishnan, Gautam Panda
Summary: Novel chemical compounds were discovered to inhibit the bc1 complex mutant of Mycobacterium tuberculosis, with two molecules showing MICs of 8 and 16 mu M, compared to MICs of 128 and 256 mu M against the wild type. These compounds were bactericidal to wild type bacteria under hypoxic conditions at concentrations much lower than their MICs, and showed synergy with an inhibitor of the bc1 complex in inhibiting bacterial growth.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Review
Chemistry, Organic
Deeksha, Ritesh Singh
Summary: Aza-oxyallyl cations have diverse reactivity profiles for constructing N-scaffolds of biological interest and recent studies have reported new variations in their reactivity, making them versatile tools for organic synthesis.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Kasim Ali, Gautam Panda
Summary: An efficient transition-metal-free multicomponent approach to the regioselective synthesis of highly substituted N-alkylpyrazoles through 1,6-addition of pyrazole (in situ generated from alpha,beta-unsaturated aldehyde and hydrazide) to para-Quinone Methides has been developed. The N-alkylpyrazole containing triarylmethanes having several heteroaryl rings (quinoline, pyridine, thiophene) at the central methine carbon atom was developed. This chemical process may be used for large-scale synthesis and provides a novel way to produce triarylmethanes with diverse functional groups.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Review
Chemistry, Medicinal
Indranil Chatterjee, Kasim Ali, Gautam Panda
Summary: This review critically analyzes the synthetic strategies and anticancer activities of benzoxazines and benzoxazepines compounds reported from 2010 onwards. The structure-activity relationship of the benzoxazine and benzoxazepine scaffolds containing bioactive compounds is also studied, focusing on how structural modification affects their anticancer activity.
Review
Chemistry, Multidisciplinary
Arpita Banerjee, Indranil Chatterjee, Gautam Panda
Summary: This article discusses the significance of tyrosine as a chiral pool in the synthesis of alkaloids, and compares synthetic steps, overall yield, and other factors between tyrosine-based and non-tyrosine-based routes.
Article
Chemistry, Multidisciplinary
Saroj Maji, Souvik Barman, Gautam Panda
Summary: In this study, a novel synthetic route towards nintedanib was developed using a stereoselective intramolecular cyclization strategy to convert beta-keto amide into a 3-acyloxindole derivative, an important scaffold for nintedanib synthesis. The condensation of the oxindole scaffold with a synthesized amine derivative led to the successful synthesis of nintedanib.
Article
Chemistry, Organic
Indranil Chatterjee, Gautam Panda
Summary: This paper describes a palladium-catalyzed regioselective reaction of propargylic carbonate with thiophenols and benzene selenol. The addition of thiols to propargylic carbonates provides an atom-economic and effective process. The reaction proceeds through hydrothiolation to produce mono(arylthiol) alkenes and hydrothiolation followed by Tsuji-Trost type substitution to form bis(arylthiol) alkenes by controlling the equivalence of thiophenols. This coupling reaction exhibits good tolerance towards functional groups and leads to the formation of highly functionalized alkenylation products via the formation of new C-S and C-Se bonds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Kasim Ali, Indranil Chatterjee, Gautam Panda
Summary: A simple and efficient metal-free approach was developed for synthesizing 4-thio-substituted chroman and diarylmethyl thioethers, providing good yields and tolerance for labile functional groups. This method is applicable to large-scale synthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Kasim Ali, Gurudayal Prajapati, Ravi Sankar Ampapathi, Gautam Panda
Summary: The reductive coupling between allylic sulfonylhydrazones and aryl boronic acids can efficiently generate 1,3-diarylpropene systems under mild reaction conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Arpita Banerjee, Gautam Panda
Summary: In this study, a base mediated, transition metal-free intermolecular epoxide ring opening reaction followed by intramolecular aromatic nucleophilic substitution (SNAr) was developed to synthesize separable diastereomers of selected benzo[b][1,4,5]oxathiazepine 1-oxides. This strategy allows the formation of both C-N and C-O bonds simultaneously in a single step. The method has a wide substrate scope, uses simple reaction conditions, and is applicable for synthesizing bioactive molecules with similar skeletons as benzoxathiazepine 1-oxides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Kasim Ali, Prajjval Mishra, Awnish Kumar, Damodara N. Reddy, Sushobhan Chowdhury, Gautam Panda
Summary: In this article, the synthesis, structure-reactivity relationships, and synthetic applications of quinone methides are discussed. The formation of intermediates during bioactivation and potential chemical manifestations leading to toxicity in biological systems are also covered.
CHEMICAL COMMUNICATIONS
(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)
