Article
Chemistry, Organic
P. Veeraraghavan Ramachandran, Shivani Choudhary
Summary: Monotrifluoroacetoxyborane-amines are efficient reagents for the one-pot, tandem reductive amination/alkylation-cycloamidation of keto or amino acids to achieve the synthesis of 5-aryl or 5-methyl pyrrolidin-2-ones and 6-aryl or 6-methyl piperidin-2-ones.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Juan Wang, Linying Wang, Dali Zhu, Wenhao Cui, Peng Tian, Zhongmin Liu
Summary: Na+-free Cu-SSZ-13 zeolites were successfully synthesized using a cooperative strategy, showing advantages of rapid crystallization and high yield. The calcined materials exhibited good NH3-SCR catalytic performance and hydrothermal stability.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Physical
Ilkay Gumus, Adem Ruzgar, Yasar Karatas, Mehmet Gulcan
Summary: The one-pot tandem synthesis of imines from alcohols and amines using the Au/MIL-101 catalyst has been demonstrated as an efficient, economical, and environmentally friendly approach. The catalyst showed high activity and selectivity, with the highest reported TOF values among MOF-supported Au catalysts, attributed to the synergistic effect between Au nanoparticles and Lewis acid sites in MIL-101. Mechanistic studies revealed that the Au NPs effectively activated the oxidation step while the Lewis acid sites catalyzed the condensation step, leading to excellent catalytic performance.
MOLECULAR CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Miho Kobatake, Norikazu Miyoshi, Masaharu Ueno
Summary: In this study, the formal total synthesis of riccardin C was achieved through a one-pot reaction, which involved simultaneous coupling reactions and subsequent reduction and deprotection. This method streamlined the process by eliminating the need for purification of intermediate reaction mixtures, thus saving resources and expediting the work.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Materials Science, Multidisciplinary
Naoki Onda, Ryota Sato, Junpei Kuwabara, Takeshi Yasuda, Takaki Kanbara
Summary: Polycondensation reaction of 1,2,4,5-tetrafluorobenzene (1) and 3,3'-dihexyl-2,2'-bithiophene was examined via Pd/Ag dual-catalyzed cross-dehydrogenative coupling. In situ deprotonation-metalation of 1 with Ag salt followed by transmetalation with a Pd catalyst successfully produced a cross-coupling product. The one-pot two-step reaction method effectively prevented undesired homo-coupling defects during polymerization. The resulting highly regioregular polymer exhibited a packed structure and strong fluorescence in the film state, showing potential as an emitting material in organic light-emitting diodes.
Article
Chemistry, Organic
Ravuri Srinath, Arindam Manna, Subhankar Shee, Vijay Babu Pathi, Saswati Ghosh, Krishnendu Khamaru, Nakul Chandra Maiti, Biswadip Banerji
Summary: A one-pot protocol for synthesizing tetracyclic triazole-piperazine-quinazolinone-fused N-heterocyclic scaffolds is reported, utilizing tandem click and cross-dehydrogentive coupling reactions with high atom economy. The method is highly functional group tolerable and has a broad substrate scope, with some derivatives showing strong white solid-state fluorescence.
Article
Chemistry, Multidisciplinary
Halenur Ozer, Dilan Arslan, Bengi Ozgun Ozturk
Summary: In this study, in situ formed ruthenium hydride species from Grubbs type catalysts were used as efficient catalysts for dehydrogenative alcohol coupling and sequential cross-metathesis/dehydrogenative coupling reactions. The selectivity of the catalysts can be tuned by using different bases to obtain different products. With the presence of a new ligand, the performance of the catalyst was significantly improved, yielding products in quantitative yields.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Shan Li, Lu Lei, Bin Feng, Xiaofeng Liu, Liqing Xian, Yajun Li
Summary: We developed a new method for the synthesis of benzo-fused bisimidazoles using N-iodosuccinimide (NIS)-mediated divergent and efficient tandem reaction between fluorinated propargyl amidines and aromatic o-diamines without any metal catalyst and additive under mild reaction conditions. The yields were moderate to excellent. Preliminary mechanistic studies suggested that this reaction proceeded through an intermediate of secondary amine derived from 5iodomethyl imidazole, and NIS played another role of oxidation reagent to promote the formation of a benzimidazole motif.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Norul Azilah Abdul Rahman, Najwa Asilah M. Shamsuddin, Mazni Musa, Yatimah Alias, Idris Sharif, Ahmad Husaini Mohamed, Karimah Kassim, Nur Rahimah Said
Summary: This study developed a PVA-SA-PdCl2 catalyst using an ultrasonic-assisted method, which exhibited excellent recyclability and reproducibility. The catalytic reaction achieved a 100% conversion rate when employing a 1 mmol% catalyst load, K2CO3 base, DMA solvent, and a 60 min reaction at 165 degrees C.
INORGANIC CHEMISTRY COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Mohammad Sadegh Asgari, Saeed Bahadorikhalili, Aram Ghaempanah, Parviz Rashidi Ranjbar, Rahmatollah Rahimi, Alireza Abbasi, Bagher Larijani, Mohammad Mahdavi
Summary: In this study, novel amide linked 1,2,3-triazoles containing aryloxy derivatives were synthesized efficiently via copper-catalyzed one-pot sequential reaction, with high isolated yields.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Lingyu Zhang, Songlin Zhang
Summary: An efficient method for the synthesis of 1,4-benzothiazinone-3-one derivatives via a potassium carbonate and copper-mediated C-S and C-N Ullmann coupling reaction between 2-bromothiophenol and 2-haloacetanilide is reported. This approach eliminates the need for noble metals and expensive ligands, making it a simple and cost-effective strategy.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Applied
Yu-Ri Lee, Xuan Huy Do, Seung Sang Hwang, Kyung-Youl Baek
Summary: A bifunctional zeolitic imidazolate framework catalyst with amine and sulfonic acid groups was successfully prepared through a simple two-step post-synthetic modification, showing good catalytic performance and reusability in the reaction.
Article
Chemistry, Multidisciplinary
Mina Keihanfar, Bi Bi Fatemeh Mirjalili
Summary: A new, green, and environmentally friendly protocol for synthesizing tetrahydrodipyrazolopyridine derivatives has been developed. This method offers advantages such as aqueous media, high yield, and simple work-up.
Article
Chemistry, Multidisciplinary
Gabriel Abranches Dias Castro, Sergio Antonio Fernandes
Summary: A green methodology was developed to produce 5-ethoxymethylfurfural (EMF) through a one-pot tandem reaction starting from fructose, eliminating unnecessary process steps and the isolation of intermediates. The reaction used microwave irradiation and p-sulfonic acid calix[4]arene as an organocatalyst, resulting in 88% yield of EMF.
REACTION CHEMISTRY & ENGINEERING
(2022)
Article
Chemistry, Organic
Yue-Xiao Wu, Ming-Hui Huang, Kang Peng, Zhen Shi, Er-jun Hao, Zhi-Bing Dong
Summary: An iodine-catalyzed one-pot synthesis of benzoazole-substituted thioenamines was reported. The reaction proceeds through an electrophilic substitution pathway in a cross dehydrogenation coupling manner. The protocol is metal-free, easy to perform, tolerates various functional groups, and provides good yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yuki Sato, Misaki Nishimura, Shin-ichi Kawaguchi, Akihiro Nomoto, Akiya Ogawa
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Review
Chemistry, Organic
Shin-ichi Kawaguchi, Akiya Ogawa
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Review
Chemistry, Organic
Yuki Yamamoto, Shin-ichi Kawaguchi, Shintaro Kodama, Akihiro Nomoto, Akiya Ogawa
CURRENT ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Cong Chi Tran, Shin-ichi Kawaguchi, Fumiya Sato, Akihiro Nomoto, Akiya Ogawa
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Tsuyoshi Douchi, Masahiro Akitake, Motohiro Sonoda, Yasumasa Sugiyama, Shinji Tanimori
SYNTHETIC COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Kento Tokumoto, Kouhei Makiyama, Motohiro Sonoda, Shinji Tanimori
Summary: The facile and general transition-metal-free access to 1-substituted-4-quinazolinones was achieved through proline-mediated cyclization, with potential pathways including radical intermediates and SNAr route. The gram-scale synthesis of 1-phenyl-4-quinazolinone was also successfully demonstrated without loss of efficiency.
Article
Chemistry, Physical
Shintaro Kodama, Yuki Yamamoto, Yohsuke Kobiki, Hitomi Matsubara, Cong Chi Tran, Shin-ichi Kawaguchi, Akihiro Nomoto, Akiya Ogawa
Summary: The study showed that the use of different transition metal catalysts can selectively synthesize different products, while also achieving a cascade synthesis from diarylation reactions to quinoxaline compounds.
Article
Biochemistry & Molecular Biology
Kento Sonoda, Saki Ujike, Akito Katayama, Norio Suzuki, Shin-ichi Kawaguchi, Tadayuki Tsujita
Summary: In this study, a higher lipophilic derivative of PyrzA was synthesized and evaluated, showing higher HIF activity and stabilizing ability at low concentrations compared to the commercially available HIF activator Roxadustat.
BIOORGANIC & MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Organic
Motohiro Sonoda, Yusuke Mimura, Shizuki Noda, Atsushi Okazawa
Summary: Aryloxyacetylthiourea and its derivatives were synthesized using commercially available phenols, 2-chloroacetamide, and N-aryl isothiocyanates. The byproducts obtained in this process were found to have bioactive properties. A one-pot synthesis method for PI-28 derivatives with comparable overall yields was also developed.
Correction
Chemistry, Medicinal
Kento Sonoda, Sudarma Bogahawaththa, Akito Katayama, Saki Ujike, Sae Kuroki, Naho Kitagawa, Kohichi Hirotsuru, Norio Suzuki, Toshio Miyata, Shin-ichi Kawaguchi, Tadayuki Tsujita
ACS PHARMACOLOGY & TRANSLATIONAL SCIENCE
(2022)
Article
Chemistry, Medicinal
Kento Sonoda, Sudarma Bogahawatta, Akito Katayama, Saki Ujike, Sae Kuroki, Naho Kitagawa, Kohichi Hirotsuru, Norio Suzuki, Toshio Miyata, Shin-ichi Kawaguchi, Tadayuki Tsujita
Summary: HIF-alpha activation has shown promising results in treating ischemic diseases. Many existing activators stabilize HIF-alpha by displacing 2-OG from PHDs. However, their specificity is low. In this study, a novel HIF activator called PyrzA was identified, which does not contain a 2-OG scaffold. PyrzA enhances HIF-alpha stability and upregulates the expression of HIF target genes. Interestingly, PyrzA decreases HIF-1 alpha prolyl hydroxylation, suggesting a novel mechanism for HIF activation.
ACS PHARMACOLOGY & TRANSLATIONAL SCIENCE
(2022)
Article
Chemistry, Organic
Takahito Uemura, Yusuke Saito, Motohiro Sonoda, Shinji Tanimori
Summary: Equol, a nonsteroidal estrogen, has been synthesized in enantioenriched forms based on MacMillan's alpha-arylation of carbonyl compound mediated by amino acid derived indazolidinones and copper precatalysts. The natural form of (S)-equol and its enantiomer (R)-equol have been successfully synthesized from 2,4-dimethoxybenzaldehyde with good enantiomeric purity (90% ee and 90% ee, respectively).
Article
Chemistry, Organic
Yuki Yamamoto, Shin-ichi Kawaguchi, Misaki Nishimura, Yuki Sato, Yoshihisa Shimada, Akihiro Tabuchi, Akihiro Nomoto, Akiya Ogawa
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Yuki Yamamoto, Ryo Tanaka, Miyuto Ota, Misaki Nishimura, Cong Chi Tran, Shin-ichi Kawaguchi, Shintaro Kodama, Akihiro Nomoto, Akiya Ogawa
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Haruna Nariki, Takuya Miyamura, Daiki Matsui, Motohiro Sonoda, Shinji Tanimori
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)