Article
Chemistry, Organic
Shu-Jie Chen, Zhi-Qing He, Guo-Shu Chen, Cheng Zhao, Chang-Ping Chen, Yin-Yin Zhuang, Long Chen, Yun-Lin Liu
Summary: A new class of Michael acceptors, tetrazolyl-trifluor-omethyl alkenes, has been discovered. They undergo Michael-type addition with aliphatic amines and azoles to produce beta-trifluoromethyl alkylamines and CF3- substituted 1,2-bisazole derivatives, respectively. Some of the products can also undergo microwave-assisted intramolecular denitrogenative annulation, leading to the formation of CF3-substituted 1,4,5,6-tetrahydro-1,2,4-triazines.
Article
Chemistry, Applied
Dae Kyum Kim, Jeong-Yu Son, Ilyong Jung, Namrim Heo, Sang Hoon Han, Dongwook Kim, Phil Ho Lee
Summary: Metal-free reaction of indoloazomethine ylides with 2-(trimethylsilyl)aryl triflates in the presence of TMAF and MeOH provided 1,4-thiadiazepines through N-arylation and intramolecular imine addition reaction, oxidized with p-chloranil. These compounds smoothly isomerized to indoloindolizines in quantitative yield, with access from indoloazomethine ylide and 2-(trimethylsilyl)aryl triflate in semi-one-pot.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Nicolas Gigant, Emmanuelle Drege, Delphine Joseph
Summary: This research achieves a Rauhut-Currier reaction cascade with carbon nucleophiles under mild conditions, enabling an efficient one-pot synthesis of densely substituted carbocycles from readily accessible substrates. The key promoter role of the cesium cation in the cascade process is demonstrated.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Natalie C. Ulrich, Jose S. Yu, David F. Wiemer
Summary: The efficiency of cationic cascade cyclizations can be enhanced by using MOM enol ethers derived from B-keto esters. The stereochemistry of the enol ethers determines the formation of the major product in geranyl and farnesyl derivatives. These cyclizations faithfully expand the stereochemistry of the original epoxide into multiple stereocenters, offering the potential to generate complex structures from simple starting materials.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Physical
Yun Ding, Hailong Ma, Baojun Li, Jianfeng Ma, Zhehao Hu, Yipeng Zhang, Xuhaoxi Wen, Aiguo Hu
Summary: The study proposed an alternative reaction mechanism by converting inactive enediynes into enyne-allenes through 1,4-Michael addition to trigger low barrier cyclization. This mechanism may play an important role in the design of structurally simple acyclic enediynes.
CHEMICAL PHYSICS LETTERS
(2021)
Article
Chemistry, Organic
Qianding Zeng, Ying Liu, Jingjing He, Yupian Deng, Pai Zheng, Zhudi Sun, Song Cao
Summary: A practical and efficient solvent-free synthesis of beta-trifluoromethyl-substituted phosphonates and phosphine oxides via hydrophosphonylation and hydrophosphinylation of alpha-(trifluoromethyl)styrenes with H-phosphonates and H-phosphine oxides, respectively, was developed. The reaction proceeded smoothly within 2 h at room temperature without the cleavage of the rather fragile C-F bond in alpha-(trifluoromethyl)styrenes and afforded a wide variety of structurally diverse and valuable beta-trifluoromethyl-containing phosphonates and phosphine oxides in moderate to good yields. This protocol features mild conditions, wide substrate scope, simple manipulation, and excellent functional group compatibility.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Shan-Shan Li, Li-Li Zhao, Min Pan, Na Feng, Jin-Bao Peng, Ai-Jun Ma
Summary: A potassium carbonate promoted tandem oxy-Michael addition/cyclization reaction has been developed for the synthesis of diverse substituted naphthopyrans. The use of readily available and inexpensive potassium carbonate as a promoter offers an efficient and sustainable approach to prepare 2-substituted naphthopyrans.
Article
Chemistry, Multidisciplinary
Li-Xia Liu, Yu-Qing Bai, Xiang Li, Chang-Bin Yu, Yong-Gui Zhou
Summary: Combining base-promoted retro-sulfa-Michael addition with palladium-catalyzed asymmetric allenylic alkylation, a streamlined synthesis of chiral thiochromanones containing two central chiralities (including a quaternary stereogenic center) and an axial chirality (allene unit) was successfully achieved, with yields up to 98%, dr of 49.0:1, and >99% ee.
Article
Materials Science, Multidisciplinary
David Edinger, Hansjoerg Weber, Ema Zagar, David Pahovnik, Christian Slugovc
Summary: The melt polymerization of acrylamide initiated by nucleophiles allows for the preparation of polyamide 3 (PA 3) with a branching factor of about 1.5. The high share of branching units imparts a fully amorphous morphology featuring a low glass-transition temperature of 67 degrees C and renders the polymer water-soluble. The polymerization mechanism can be considered as an aza-Michael polymerization involving zwitterionic species as key intermediates, with the highest branching obtained at 83 degrees C.
ACS APPLIED POLYMER MATERIALS
(2021)
Article
Chemistry, Applied
Navpreet Kaur, Priyanka Singh, Prabal Banerjee
Summary: An efficient protocol for the synthesis of spiro-imidazolidinone-cyclohexadienones from p-quinone methides and dialkyloxy ureas is reported, showing good functional group tolerance and providing a straightforward method for accessing the desired compounds. Additionally, the debenzylation of spiroimidazolidinones to give N-hydroxycyclic ureas has been demonstrated in follow-up chemistry.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Inavolu Vani, Reddymasu Sireesha, Palle Vinod Kumar Goud, Kottapalli Rajasekhara Prasad, Mandava Bhuvan Tej, Muthineni Sai Praneeth, Mandava Venkata Basaveswara Rao
Summary: A series of nitroethylindole derivatives were synthesized via Michael addition reaction between Indole and substituted nitrostyrenes, characterized by H-1 NMR, C-13 NMR, and LC-MS analysis.
POLYCYCLIC AROMATIC COMPOUNDS
(2022)
Article
Biochemistry & Molecular Biology
Saman Sayebani, Hossein Eshghi, Maryam Naeimabadi
Summary: A new and diverse route has been developed for synthesis of novel pyrrole derivatives using azomethine ylides. The azomethine ylides are produced via C-H activation and then reacted with olefins to form pyrrole derivatives. This synthetic method shows moderate to excellent yields in experiments.
MOLECULAR DIVERSITY
(2022)
Article
Chemistry, Multidisciplinary
Hongkun Xu, Xuan Qin, Yaping Zhang, Chuan Wan, Rui Wang, Zhanfeng Hou, Xiaofeng Ding, Hailing Chen, Ziyuan Zhou, Yang Li, Chenshan Lian, Feng Yin, Zigang Li
Summary: The modification and functionalization of peptides play a crucial role in biotechnology and drug development. A highly reactive Michael-type warhead is reported here for the covalent modification of cysteine on peptides and proteins. By incorporating a vinyl group onto a methionine residue, the resulting vinyl sulfonium can be efficiently nucleophilically added by a suitable cysteine residue, leading to the formation of cyclized peptides. This peptide cyclization strategy demonstrates improved cell penetration and stability. Furthermore, a peptide ligand containing vinyl sulfonium can covalently bind to cysteine in the target protein, indicating the potential of vinyl sulfonium as a novel warhead for developing covalent peptide inhibitors.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Organic
Daiki Ishii, Shin-ichi Hirashima, Kosuke Nakashima, Hiroshi Akutsu, Takaaki Sakai, Yasuyuki Matsushima, Masahiro Kawada, Tsuyoshi Miura
Summary: A new organocatalyst efficiently promotes the asymmetric direct vinylogous conjugate additions of alpha-angelica lactones to benzoyl acrylonitrile derivatives, resulting in products with excellent enantioselectivities. The chiral gamma,gamma-disubstituted gamma-butenolides obtained can be readily transformed to valuable synthetic intermediates.
Article
Chemistry, Multidisciplinary
He Liu, Zhiwen Liu, Ganggang Li, Huaina Huang, Changjiang Zhou, Zhiming Wang, Chuluo Yang
Summary: A simple acid-catalyzed solvent-free metal-free cyclization method between diarylamines and ketones is proposed to construct SpAs, providing a wide range of possibilities for efficient TADF emitters. By applying D2T-TR in OLEDs, a maximum external quantum efficiency of 27.1% is achieved, demonstrating the potential of this method for developing excellent organic optoelectronic materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
Maoyuan Tian, Taoling Zeng, Mingdong Liu, Shang Han, Huayue Lin, Qi Lin, Li Li, Tingting Jiang, Gao Li, Hong Lin, Ting Zhang, Qiaofeng Kang, Xianming Deng, Hong-Rui Wang
JOURNAL OF BIOLOGICAL CHEMISTRY
(2019)
Article
Biochemistry & Molecular Biology
Chengqian Yin, Bo Zhu, Ting Zhang, Tongzheng Liu, Shuyang Chen, Yu Liu, Xin Li, Xiao Miao, Shanshan Li, Xia Mi, Jie Zhang, Li Li, Guo Wei, Zhi-xiang Xu, Xiumei Gao, Canhua Huang, Zhi Wei, Colin R. Goding, Peng Wang, Xianming Deng, Rutao Cui
Article
Multidisciplinary Sciences
Caixia Yang, Xin Pang, Weihai Chen, Xiaoyong Wang, Gan Lin, Chengchao Chu, Xianzheng Zhang, Xianming Deng, Xiaoyuan Chen, Gang Liu
Article
Pharmacology & Pharmacy
Fu Gui, Jie Jiang, Zhixiang He, Li Li, Yunzhan Li, Zhou Deng, Yue Lu, Xinrui Wu, Guyue Chen, Jingyi Su, Siyang Song, Yue-Ming Zhang, Cai-Hong Yun, Xin Huang, Ellen Weisberg, Jianming Zhang, Xianming Deng
BRITISH JOURNAL OF PHARMACOLOGY
(2019)
Article
Multidisciplinary Sciences
Jinwei Zhang, Mohammad Iqbal H. Bhuiyan, Ting Zhang, Jason K. Karimy, Zhijuan Wu, Victoria M. Fiesler, Jingfang Zhang, Huachen Huang, Md Nabiul Hasan, Anna E. Skrzypiec, Mariusz Mucha, Daniel Duran, Wei Huang, Robert Pawlak, Lesley M. Foley, T. Kevin Hitchens, Margaret B. Minnigh, Samuel M. Poloyac, Seth L. Alper, Bradley J. Molyneaux, Andrew J. Trevelyan, Kristopher T. Kahle, Dandan Sun, Xianming Deng
NATURE COMMUNICATIONS
(2020)
Article
Chemistry, Medicinal
Yun Chen, Hongbin He, Hua Jiang, Li Li, Zhiyu Hu, Huiying Huang, Qingyan Xu, Rongbin Zhou, Xianming Deng
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2020)
Article
Chemistry, Organic
Lei Zhang, Yuezhou Wang, Wei Huang, Yanling Wei, Zile Jiang, Lulin Kong, An-an Wu, Zhiyu Hu, Huiying Huang, Qingyan Xu, Li Li, Xianming Deng
Article
Chemistry, Medicinal
Zhou Deng, Guyue Chen, Shuang Liu, Yunzhan Li, Jiaji Zhong, Baoding Zhang, Li Li, Huiying Huang, Zheng Wang, Qingyan Xu, Xianming Deng
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2020)
Article
Biochemistry & Molecular Biology
Wenjuan Li, Hengxiao Ni, Shaofeng Wu, Shang Han, Chang'an Chen, Li Li, Yunzhan Li, Fu Gui, Jiahuai Han, Xianming Deng
Article
Chemistry, Medicinal
Fleur M. Ferguson, Yan Liu, Wayne Harshbarger, Ling Huang, Jinhua Wang, Xianming Deng, Stephen J. Capuzzi, Eugene N. Muratov, Alexander Tropsha, Senthil Muthuswamy, Kenneth D. Westover, Nathanael S. Gray
JOURNAL OF MEDICINAL CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Yunzhan Li, Zehua Liu, Li Li, Wenhua Lian, Yaohui He, Elbadry Khalil, Ermei Makila, Wenzhong Zhang, Giulia Torrieri, Xueyan Liu, Jingyi Su, Yuanming Xiu, Flavia Fontana, Jarno Solonen, Jouni Hirvonen, Wen Liu, Hongbo Zhang, Helder A. Santos, Xianming Deng
Article
Chemistry, Medicinal
Xiaoyang Li, Jingyi Su, Yanru Yang, Wenhua Lian, Zhou Deng, Zaiyou Yang, Guyue Chen, Baoding Zhang, Chao Dong, Xueyan Liu, Li Li, Zheng Wang, Zhiyu Hu, Qingyan Xu, Xianming Deng
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2020)
Article
Biochemistry & Molecular Biology
Yuezhou Wang, Lei Zhang, Yanling Wei, Wei Huang, Li Li, An-an Wu, Anahita Dastur, Patricia Greninger, Walter M. Bray, Chen-Song Zhang, Mengqi Li, Wenhua Lian, Zhiyu Hu, Xiaoyong Wang, Gang Liu, Luming Yao, Jih-Hwa Guh, Lanfen Chen, Hong-Rui Wang, Dawang Zhou, Sheng-Cai Lin, Qingyan Xu, Yuemao Shen, Jianming Zhang, Melissa S. Jurica, Cyril H. Benes, Xianming Deng
CELL CHEMICAL BIOLOGY
(2020)
Article
Chemistry, Multidisciplinary
Long Li, Xin-Qi Zhu, Ying-Qi Zhang, Hao-Zhen Bu, Peng Yuan, Jinyu Chen, Jingyi Su, Xianming Deng, Long-Wu Ye
Article
Chemistry, Multidisciplinary
Zehua Liu, Yunzhan Li, Wei Li, Wenhua Lian, Marianna Kemell, Sami Hietala, Patricia Figueiredo, Li Li, Ermei Makila, Ming Ma, Jarno Salonen, Jouni T. Hirvonen, Dongfei Liu, Hongbo Zhang, Xianming Deng, Helder A. Santos
MATERIALS HORIZONS
(2019)