Article
Chemistry, Organic
Jie Yang, Lizhi Gai, Xiaoyang Chen, Yanfei Liu, Shengmei Wu, Jiao Feng, Xinbing Sui, Hua Lu
Summary: This study synthesized dyes with stable seven-membered N,O-boron-chelated skeleton and thoroughly investigated their photophysical properties through spectroscopic tests and theoretical calculations. Single-crystal X-ray diffraction studies provided evidence of their structure. These dyes produced singlet oxygen species under laser irradiation, showing potential as photosensitizers for treating superficial tumors.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Shuyou Chen, Delong Mu, Pei-Lin Mai, Jie Ke, Yingzi Li, Chuan He
Summary: The authors present a rhodium-catalyzed enantioselective synthesis of six- and seven-membered tri-organosubstituted silicon-stereogenic heterocycles, which significantly expand the chemical space of silicon-centered chiral molecules and show potential application prospects in the field of organic optoelectronic materials.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Hiroki Saito, Ranmaru Kato, Kazutada Ikeuchi, Takahiro Suzuki, Keiji Tanino
Summary: An anionic 8 pi electrocyclic reaction of 4-(diethoxyphosphoryl)-1,3,6-heptatriene derivatives was developed, where the substrate underwent deprotonation followed by the 8 pi electrocyclization. The subsequent Horner-Wadsworth-Emmons reaction in one pot resulted in the production of the target product, a 3-alkylidene1,4-cycloheptadiene derivative. The electrocyclic reaction proceeded in a stereospecific manner, leading to the stereocontrolled formation of two neighboring stereogenic centers.
Article
Chemistry, Organic
Jordi Vila, Miquel Sola, Anna Pla-Quintana, Anna Roglans
Summary: The synthesis of spiro compounds with seven- and six-membered rings was achieved through a cascade process involving a rhodium(I)-catalyzed cycloisomerization and a highly selective Diels-Alder homodimerization. The scope of the reaction was analyzed using synthetic substrates, and control experiments and DFT calculations were used to explain the observed degree of selectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Kaoru Funaki, Hidetsugu Tabata, Yusuke Nakazato, Yuka Takahashi, Tomohiko Tasaka, Hideyo Takahashi, Hideaki Natsugari, Tetsuta Oshitari
Summary: By performing the 5N-acylation reaction on 1N-methyl-1,5-benzodiazepin-2ones using (S)-2-phenylpropanoyl and (S)-2-phenylbutanoyl chlorides, the (a1S,a2S,S)-atropisomer (I) was obtained with high diastereoselectivity over the (a1R,a2R,S)-isomer (II). The preferential formation of I can be attributed to the thermodynamically preferable pi-pi stacking interaction between two benzene rings in the benzodiazepine ring and the acyl chloride during the reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Sheersha Pradhan, Panneerselvam Muthuvel, Thangamuthu Mohan Das
Summary: The development of benzothiazepine, a seven-membered heterocyclic scaffold, has gained recognition due to its medicinal relevance in mild environmentally friendly conditions. A novel class of [1,5]-benzothiazepine-C-fi-D-glycosides was synthesized from a, fi-unsaturated -b-C-glycosidic ketones using a one-pot method. The fi-anomeric forms of the C-glycosidic compounds were determined by 1H NMR spectroscopy. The [1,5]-benzothiazepine-based fi-C-glycosides exhibited moderate antioxidant activities, with a maximum inhibitory activity of 60%.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Review
Chemistry, Organic
Lillian A. de Ceuninck van Capelle, James M. Macdonald, Christopher J. T. Hyland
Summary: This review discusses the conformational and stereochemical properties of medium-ring benzo-fused N-heterocycles, highlighting the impact of different structural factors on the atropisomeric nature of these compounds. It serves as a valuable resource for the design, synthesis, and study of new and potentially bioactive compounds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Maxim Andreev, Vyacheslav S. Bogdanov, Mikhail A. Frolov, Alexander F. Smol'yakov, Vladimir V. Burlakov
Summary: The interaction between the seven-membered zirconacyclocumulene complex and acenaphthenequinone leads to the formation of cyclobutadiene and its subsequent dimerization in cyclooctatetraene, along with the formation of a tetraoxadizirconacycle consisting of two zirconocene and two acenaphthenequinone fragments. When this reaction occurs in the presence of excess cyclopentadiene or acenaphthylene, the cyclobutadiene is trapped by the Diels-Alder reaction. Cyclobutadiene can act as both a dienophile and a diene source in these reactions.
