Article
Chemistry, Organic
Raghuramaiah Mandadapu, Amol Satish Dehade, Shrikant Abhiman Shete, Mark Montgomery, Vikas Sikervar, Ravindra Sonawane
Summary: Two different Lewis acids were utilized to achieve regioselective [3+2] and [3+3] cycloaddition reactions of an azomethine imine with activated cyclopropanes, resulting in moderate yields of tetrahydropyrazolone derivatives and tricyclic tetrahydrofuran derivatives as well as high regioselectivity in forming hexahydropyridazinone derivatives.
SYNTHESIS-STUTTGART
(2021)
Article
Biochemistry & Molecular Biology
Guosheng Yang, Sicheng Li, Qiumi Wang, Huabao Chen, Chunping Yang, Zhongqiong Yin, Xu Song, Li Zhang, Cuifen Lu, Guizhou Yue
Summary: The synthesis of dicyclic spiropyridazine oxoindole derivatives by [3+3]-cycloaddition reaction of N-unsubstituted isatin N,N'-cyclic azomethine imine 1,3-dipoles was successfully achieved. The products, having two consecutive stereocenters including spiroquaternary stereocenters in one ring structure, were obtained in moderate to excellent yields (20-93%) and low to moderate diastereoselectivities (1:9-10:1 dr). The synthesized compounds were thoroughly characterized using various spectroscopic techniques.
Article
Chemistry, Organic
Mamta Gill, Arko Das, Vinod K. Singh
Summary: An enantioselective (3+2) cycloaddition reaction has been reported for the synthesis of chiral polysubstituted pyrrolidines. The reaction displays opposite regioselectivity with excellent enantioselectivities and yields. Interestingly, changing the alpha-substituents of the iminoesters results in the formation of normal (3+2) cycloaddition products with excellent enantioselectivities as well.
Article
Chemistry, Organic
Zhaoqi Wu, Heng Wang, Tianci Chen, Ze-Feng Xu, Chuan-Ying Li
Summary: We present a rhodium-catalyzed intramolecular [4 + 3] cycloaddition reaction of 1-sulfonyl-1,2,3-triazoles, providing an efficient approach for the synthesis of cyclobutane-fused dihydroazepines with moderate to good yields. Furthermore, the reaction enables the construction of three stereocenters, leading to the formation of a single diastereomer in each case. The stereoselectivity control is also discussed.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Organic
Kelvin J. Y. Wu, Amy E. Benedetto, Andrew G. Myers
Summary: The regioselectivity of a [3+2] dipolar cycloaddition reaction between a stabilized azomethine ylide and an electron-deficient dipolarophile is contrary to a previous report in this journal.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Sundaravel Vivek Kumar, Patrick J. Guiry
Summary: Asymmetric [3+2] cycloaddition reactions are interesting methods for synthesizing enantioenriched pyrrolidines with up to four stereocentres. Pyrrolidines are important compounds in biology and organocatalytic applications. This review summarizes the recent advancements in the enantioselective synthesis of pyrrolidines using metal catalysis, focusing on the [3+2] cycloadditions of azomethine ylides. The reactions are organized based on the type of metal catalysis and the complexity of the dipolarophile, highlighting their advantages and limitations.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Jose Cortes Vazquez, Jacqkis Davis, Vladimir N. Nesterov, Hong Wang, Weiwei Luo
Summary: A formal [3 + 3] cyclization reaction has been developed for the synthesis of 1,3,4-oxadiazinanes with generally high yields (up to 96%). The reaction, catalyzed by Sc(OTf)(3), has a broad substrate scope for both diaziridines and quinones. The synergistic activation of 1,3-dipolar diaziridines and dipolar quinones was found to be essential for enabling this reaction.
Article
Chemistry, Multidisciplinary
Sha Li, Yahan Sun, Xiaofang Li, Oskar Smaga, Sebastian Koniarz, Marcin Stepien, Piotr J. Chmielewski
Summary: A 1,3-cycloaddition reaction between 2-(tert-butyl)-8H-isoquinolino[4,3,2-de]phenanthridin-9-ium chloride and Ni-II norcorrole in the presence of base has been demonstrated to yield a family of chiral derivatives fused with pyrrole subunits of the macrocycle. Dehydrogenation of the cycloaddition products leads to dibenzoullazine ortho-fused antiaromatic porphyrinoids.
CHEMICAL COMMUNICATIONS
(2022)
Article
Biochemistry & Molecular Biology
Qiumi Wang, Sicheng Li, Guosheng Yang, Xinyu Zou, Xi Yin, Juhua Feng, Huabao Chen, Chunping Yang, Li Zhang, Cuifen Lu, Guizhou Yue
Summary: The allylation of N-unsubstituted isatin N,N'-cyclic azomethine imines with Morita-Baylis-Hillman carbonates in the presence of 1-10 mol% DABCO in DCM at room temperature resulted in the rapid formation of N-allylated and N, beta-diallylated isatin N,N'-cyclic azomethine imine 1,3-dipoles in moderate to high yields. This reaction offers mild reaction conditions, practical operability, and short reaction times in most cases. Furthermore, the alkylated products can be transformed into novel bicyclic spiropyrrolidine oxoindole derivatives through [3+2] or [3+3]-cycloaddition reactions with maleimides or Knoevenagel adducts.
Article
Chemistry, Multidisciplinary
Vladimir A. Motornov, Andrey A. Tabolin, Sema L. Ioffe
Summary: A facile and versatile method for the synthesis of [5,5]-annulated N-fused heterocycles, pyrrolo[2,1-b]thiazoles and pyrrolo[1,2-b]indazoles, via oxidative [3+2] annulation of nitroalkenes and azolium ylides in the presence of copper(ii) has been developed. The reaction is performed under mild conditions using copper(ii) trifluoroacetate/2,6-lutidine system and gives moderate to good yields of the target N-fused heterocycles. Unique fluorinated derivatives can also be accessed using this methodology with alpha-fluoronitroalkenes.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Applied
Qi Huang, Chuanjiang Xiong, Yungui Peng
Summary: A diastereoselective (3+3) cycloaddition of azomethine imines and in situ-generated azaoxyallyl cations from a-halohydroxamate promoted by a Bronsted base has been developed. A series of pyrazolo [1,2-a][1,2,4]triazin-6-ones were accessed with up to 95% yields and diastereoselectivities greater than 20:1. The asymmetric version of this reaction was explored and moderate enantioselectivity was achieved after screening a series of cinchonine-derived chiral catalysts.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Nan Ren, Lingfeng Zhang, Yijie Hu, Xiaoli Wang, Zhen Deng, Jie Chen, Hongmei Deng, Hui Zhang, Xiao-Jun Tang, Weiguo Cao
Summary: By using methyl beta-perfluoroalkylpropionate as the Michael acceptor, an efficient approach for synthesizing perfluoroalkylated pyrrolidine-fused coumarins has been achieved. The enhanced electrophilicity resulting from the strong electron-withdrawing ability of the perfluoroalkyl group is crucial for this tandem reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Ruo-Qing Wang, Chong Shen, Xiang Cheng, Xiu-Qin Dong, Chun-Jiang Wang
Summary: In this study, copper-catalyzed asymmetric propargylic substitution was successfully achieved using salicylaldehyde-derived imine esters and propargylic carbonates, resulting in a wide range of chiral amino acid derivatives containing propargylic groups. The ortho-hydroxy group of the salicylaldehyde-derived imine esters played a crucial role in increasing reactivity and stabilizing the azomethine ylide.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Vladimir Savych, Vladimir L. Mykhalchuk, Pavlo Melnychuk, Andrii O. Isakov, Taras Savchuk, Vadim M. Timoshenko, Sergiy A. Siry, Sergiy O. Pavlenko, Dmytro Kovalenko, Oleksandr Hryshchuk, Vitalii A. Reznik, Bohdan A. Chalyk, Vladimir S. Yarmolchuk, Eduard B. Rusanov, Pavel K. Mykhailiuk
Summary: A general approach for the synthesis of bicyclic fused pyrrolidines was elaborated using a [3 + 2]-cycloaddition reaction between nonstabilized azomethyne ylide and electron-deficient alkenes. The reaction conditions were optimized to enable the synthesis of novel molecules, including medicinally relevant pyrrolidine derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yoshihiko Yamamoto, Syunji Tazawa, Ryu Tadano, Takeshi Yasui
Summary: Despite advances in trifluoromethylation methods, synthesizing complex trifluoromethylated molecules with a natural-product-like 3D structure is still challenging. This study investigated the cycloaddition of novel CF3-substituted oxidopyridinium betaines. By methylating trifluoromethylated pyridin-3-ols and reacting the generated pyridinium ions with triethylamine and N-methylmaleimide, trifluoromethylated 8-azabicyclo[3.2.1]octane derivatives were produced through a (5+2) cycloaddition. The regioselectivity and stereoselectivity of the reactions depended on the positions of the CF3 substituents, and computational investigations were conducted to gain further insight into the reactivity of trifluoromethylated oxidopyridinium betaines.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Biochemistry & Molecular Biology
Jia Liu, Honglian Li, Chao Zheng, Shichao Lu, Xianru Guo, Xinming Yin, Risong Na, Bin Yu, Min Wang
Article
Optics
Yi Wang, Jia Liu, Meiqing Zhu, Lijun Wang, Xianyang Zen, Shisuo Fan, Zhen Wang, Honglian Li, Risong Na, Xi Zhao, Qing X. Li
JOURNAL OF LUMINESCENCE
(2018)
Article
Chemistry, Organic
Chao Zheng, Wan-Min Cheng, Hong-Lian Li, Ri-Song Na, Rui Shang
Article
Agriculture, Multidisciplinary
Li An, Jingwei Ma, Dongmei Qin, Hong Wang, Yongliang Yuan, Honglian Li, Risong Na, Xujin Wu
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Meirong Song, Duan Hu, Xianfu Zheng, Lixia Wang, Zhilun Yu, Wankai An, Risong Na, Chuxin Li, Ning Li, Zhouhui Lu, Zhichao Dong, Yilin Wang, Lei Jiang
Article
Chemistry, Analytical
Meiqing Zhu, Lijun Wang, Xiaoqin Wu, Risong Na, Yi Wang, Qing X. Li, Bruce D. Hammock
ANALYTICA CHIMICA ACTA
(2019)
Article
Agriculture, Multidisciplinary
Lijun Wang, Xiaoqin Wu, Zongyuan Zhao, Fugang Fan, Meiqing Zhu, Yi Wang, Risong Na, Qing X. Li
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2020)
Article
Agriculture, Multidisciplinary
Jia Liu, Shichao Lu, Jiayang Feng, Changkai Li, Wenliang Wang, Yiming Pei, Shengli Ding, Meng Zhang, Honglian Li, Risong Na, Qing X. Li
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2020)
Review
Agronomy
Liu Xu, Yong Xie, Risong Na, Qing X. Li
PEST MANAGEMENT SCIENCE
(2020)
Article
Agronomy
Changkai Li, Yuqing Wu, Xinming Yin, Zhongjun Gong, Hongxia Xing, Jin Miao, Shuzhi Wang, Jia Liu, Risong Na, Qing X. Li
Summary: This study presents a synthetic approach to produce the orange wheat blossom midge (Sitodiplosis mosellana) sex pheromones. The method achieved high enantioselectivity and overall yields in a short period, while conventional methods required longer synthesis time with lower yields. The synthesized pheromones demonstrated significant attractiveness to S. mosellana males in laboratory tests and field trials.
PEST MANAGEMENT SCIENCE
(2023)
Article
Agriculture, Multidisciplinary
Likang Zhao, Changkai Li, Meng Zhang, Honglian Li, Shengli Ding, Xi Zhao, Lianjuan Yang, Jia Liu, Qing X. Li, Risong Na
Summary: Falcarindiol analogs were designed and synthesized, and their antifungal activities were tested against eight economically significant phytopathogenic fungal species. Compound 8o exhibited the best antifungal activity against Phytophthora capsici and was 195-fold more potent than the fungicide carbendazim. The isomer (1S, 6S)-8o showed the highest antifungal activity against Monilia fructigena and P. capsici.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Youwu Hao, Di Liu, Yonghui Song, Xinming Yin, Jia Liu, Risong Na, Qing X. Li
Summary: The translocation and delivery of pesticides to their target molecules is often a limiting factor in their efficacy. Nanomaterials have provided a new approach to increase pesticide efficacy and reduce risks. In this study, a mitochondria-targeted pesticide nanocarrier was successfully synthesized, which enhanced the toxicity and efficacy of the pesticide chlorfenapyr by inducing mitochondrial damage.
ENVIRONMENTAL SCIENCE-NANO
(2022)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
