Article
Chemistry, Organic
Ying-Xian Li, Xiao-Bing Feng, Xue-Min Jia, Huang Jin, Fei Chen, Yong-Long Zhao, Ji-Quan Zhang, Jian-Ta Wang, Bing Guo, Lei Tang, Yuan-Yong Yang
Summary: A mild and green methodology was developed for regiodivergent functionalization of isoquinoline-1,3(2H,4H)-diones under aerobic conditions. Different nucleophiles led to two types of products, one thermodynamic controlled and the other kinetic controlled. The aldol type product was further transformed into benzo[c]phenanthridine core structures under transition metal free conditions, providing an environmentally benign access to this framework.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yuki Murakami, Kazuki Hisano, Hiroshi Nishino
Summary: The Mn(III)-catalyzed aerobic oxidation of methylenebis-(cyclohexane-1,3-dione) enols 1 resulted in the formation of 6a-hydroxy-2,3,4,6a,7,8,9,10a-octahydro-1H-benzo[c]chromene-1,6,10-triones 3. The proposed mechanism for the formation of 3 was supported by the isolation and transformation of intermediates 2 under Claisen and retroClaisen conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Organic
Yan-Ning Niu, Xiao-Feng Xia
Summary: In this review, we summarize the diverse range of synthetic methods employing acryloyl benzamides as key substrates to furnish isoquinoline-1,3-diones using different radical precursors, such as those containing carbon, sulphur, phosphorus, nitrogen, silicon and bromine. This will stimulate the interest of readers to engage in research in this field.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Yilin Liu, Yuming Song, Yingju Xu, Meixu Jiang, Haibin Lu
Summary: In this study, a novel series of CRBN modulators were designed and synthesised. Compound 10a showed potent antiproliferative and anti-inflammatory activity, with low toxicity to normal cells. Further studies revealed compound 10a's ability to induce apoptotic events, cell cycle arrest, and degradation of specific proteins. These findings suggest that compound 10a may be a potential antitumor drug.
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Organic
Xing-Lan Wang, Xue Bai, Chun-Feng Wu, Yong-Xi Dong, Min Zhang, Ling-Ling Fan, Lei Tang, Yuan-Yong Yang, Ji-Quan Zhang
Summary: The first direct C(sp(3))-H bond sulfonylation and sulfuration reactions of isoquinoline-1,3-(2H,4H)-diones have been developed under transition-metal-free conditions. These reactions offer high atom economy, green reaction conditions, easily accessible materials, and a broad substrate scope through a free radical reaction process.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Natarajan Tamizharasan, Gurulingappa Hallur, Palaniswamy Suresh
Summary: A novel palladium-catalyzed direct alpha-arylation of indane-1,3-dione to 2-substituted aryl/heteroaryl indene-1,3-diones was successfully developed, with Bu-t-XPhos identified as the preferred ligand. Various aryl iodides and aryl triflates with different substituents yielded high yields, facilitating the synthesis of a diverse library of alpha-arylated 1,3-diones.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Shengqing Ye, Chen Zhuang, Jiajing Lv, Chao Zhang, Qi Chen, Zhiyuan Wu, Jie Wu, Hongguang Xia
Summary: This article describes a three-component reaction of cyclobutanone oxime esters, DABCO(SO2)(2) and N-alkyl-N-methacryloyl benzamides, which can afford sulfonyl-containing isoquinoline-1,3-(2H,4H)-diones without the addition of any oxidant or transition metal.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Qin Zeng, Xinyu Huang, Mingqing Liu, Zongxiang Yu, Yuanjing Xiao
Summary: A chemodivergent tandem reaction was developed for the intermolecular hydrocarbonation and intramolecular heterocyclization of S-CF3-1,3-enyne with S-ketothioamides (KTAs), leading to the formation of ring-trifluoromethylated 4H-pyran or 4H-thiopyran. The reaction exhibited a remarkable substituent effect, with the substituents on the keto moiety or the nitrogen atom of KTAs having a significant impact on the chemoselectivity.
Article
Chemistry, Multidisciplinary
Hao Guo, Huahao Wang, Hongyi Zhao, Dongfeng Zhang
Summary: This article reports a visible light-induced diastereoselective synthesis of 4,6a-dihydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-diones using 2H-azirines and maleimides in the presence of an organic photocatalyst. The method is efficient, environmentally friendly, and shows good tolerance towards functional groups and substrates. Applications of the cycloaddition products were demonstrated through simple synthetic transformations.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Crystallography
Huixing Li, Xinlong Han, Bin Cao
Summary: The compound is C14H15F2NO2, crystallizing in monoclinic system with cell parameters a=11.5474(10) angstrom, b=11.0737(7) angstrom, c=11.4311(10) angstrom, and β=114.979(11) degrees.
ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES
(2021)
Article
Chemistry, Organic
Jiahui Fu, Xingxing Cai, Yihuo Liu, Jinghua Li, Dongping Cheng, Xiaoliang Xu
Summary: An efficient visible-light-mediated tandem reaction has been developed for the synthesis of isoquinoline-1,3(2H,4H)-diones. The reaction proceeds via radical addition and cyclization, providing a good opportunity to discover new bioactive compounds.
SYNTHESIS-STUTTGART
(2022)
Article
Engineering, Chemical
Carmellina Daniela Badiceanu, Catalina Mares, Diana Camelia Nuta, Speranta Avram, Constantin Draghici, Ana-Maria Udrea, Irina Zarafu, Cornel Chirita, Marilena Viorica Hovanet, Carmen Limban
Summary: Novel phthalimide derivatives and hexahydrophthalimide derivative have been successfully synthesized and their chemical structures were elucidated. The compounds exhibited antioxidative activity, with compound 1b being the most active. Bioinformatics analysis predicted their pharmacokinetics and pharmacodynamics profiles, showing good intestinal absorption, BBB and CNS permeabilities, and important molecular targets for antioxidant activity.
Article
Chemistry, Organic
Jiaxuan Shao, Youjia Wang, Silu Chen, Shaowei Wang, Yanhui Wu, Xulian Li, Weihua Zhang, Chao Deng
Summary: A novel visible-light and air-promoted direct radical difluoromethylation of N-benzamides has been developed for the synthesis of CF2H-containing isoquinoline-1,3-diones, representing the first metal-free catalytic synthesis of such compounds. The reaction features mild conditions, metal-free catalysis, air oxidation, and no need for additives, providing an efficient strategy for the synthesis of various CF2H-containing isoquinoline-1,3-diones.
Article
Multidisciplinary Sciences
Anis Ahamed, Ibrahim A. Arif, Radhakrishnan SurendraKumar, Idhayadhulla Akbar, Baji Shaik
Summary: This study aims to develop a new pyrimidine-2,4-dione hybrid with 2H-thiopyran molecules as potential antibacterial and antifungal agents. The synthesis of these compounds was carried out using water and an Mg(II) acetate catalyst. The antimicrobial and antifungal activities were tested, along with cytotoxic screening.
JOURNAL OF KING SAUD UNIVERSITY SCIENCE
(2023)
Article
Crystallography
Jianlian Liu, Chaojun Du, Hong Hao
Summary: The crystal structure of the substance belongs to the monoclinic system, with cell parameters a = 11.8292 Å, b = 11.0987 Å, c = 11.6480 Å, and β = 115.282 degrees, and the crystal volume is 1382.8 Å^3.
ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES
(2021)
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)