Article
Chemistry, Organic
Nagaraju Payili, Santhosh Reddy Rekula, Challa Gangu Naidu, Satyanarayana Yennam
Summary: A simple and efficient synthesis has been developed for 1,2,4-triazole derivatives with good yields using 2-arylidene-1,3-indandiones and 1-methylhydrazine-l-carbonitrile. The reactions involve formal [3 + 2] cycloaddition and skeletal rearrangement followed by T3P mediated dehydrogenative coupling. This method provides a new and useful strategy for the synthesis of novel 1,2,4-triazole derivatives.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Ranadeep Talukdar, Vikram Singh, Hemlata Mourya, Malik Nasibullah, Bhoopendra Tiwari
Summary: The new method reported in this study synthesizes 1,2,3-triazole-fused polyaromatic frameworks through a three-step reaction. Under mild conditions, the target products are obtained, along with the corresponding dihydrocarbocycles.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Tobias Sandmeier, Erick M. Carreira
Summary: The study introduces the enantio- and chemoselective N-allylation of oximes, yielding cyclic nitrones and enantioenriched aliphatic allylic alcohols through intramolecular kinetic resolution. The method stands out for its ability to utilize E/Z-isomeric oxime mixtures convergently and high functional group tolerance, showcasing its synthetic utility with the formal synthesis of (+)-halichlorine.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Shandev Pookkandam Parambil, Santhini Pulikkal Veettil, Wim Dehaen
Summary: Cycloaddition reactions are rapid and powerful tools for constructing heterocycles and carbocycles. The [3+2] cycloadditions of nitroalkenes with various 1,3-dipoles are particularly interesting to organic chemists, leading to the synthesis of N-substituted and NH-1,2,3-triazoles and other five-membered N-heterocycles.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Mei-Jun Zhu, Rong Ye, Wen-Jing Shi, Jing Sun, Chao-Guo Yan
Summary: In the presence of TEMPO as an oxidizer, a new synthetic method for functionalized spiro compounds was developed through the reaction of aldohydrazones with 2-arylidene-1,3-indnaediones or 5-arylidene-1,3-dimethylbarbituric acids.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Organic
Jian-Bin Lu, Shu-Yuan Liang, Wu-Tao Gui, Zhi-Chao Chen, Wei Du, Ying-Chun Chen
Summary: A relay catalytic protocol utilizing pyrrolidine and palladium catalysis has been developed for the asymmetric synthesis of 1,3-diamine derivatives from 3-substituted 1,3-dienes, sulfuric diamide, and aldehydes. This one-pot, three-component reaction offers the advantages of high atom step economy and operational simplicity, providing an efficient and straightforward access to valuable 1,3-diamines containing quaternary and tertiary stereogenic centers with moderate to good enantioselectivity.
Article
Chemistry, Organic
Kaili Cen, Jiahao Wei, Yuting Feng, Yuan Liu, Xinye Wang, Yangyu Liu, Yalin Yin, Junhong Yu, Dahan Wang, Jinhui Cai
Summary: This study presents a strategy for the efficient synthesis of fused 3-trifluoromethyl-1,2,4-triazoles using a triethylamine-promoted intermolecular [3 + 2] cycloaddition pathway. The method exhibits high efficiency, good functional group tolerance, mild conditions, and ease of operation. Additionally, gram-scale reactions and product derivatizations were successfully conducted, demonstrating the practicality of this approach.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Kaili Cen, Jiahao Wei, Yuting Feng, Yuan Liu, Xinye Wang, Yangyu Liu, Yalin Yin, Junhong Yu, Dahan Wang, Jinhui Cai
Summary: This article presents a facile strategy for synthesizing fused 3-trifluoromethyl-1,2,4-triazoles, which are difficult to obtain using traditional methods. The strategy involves a triethylamine-promoted intermolecular [3 + 2] cycloaddition, with yields ranging from 50% to 96%. The method is highly efficient, tolerant towards various functional groups, conducted under mild conditions, and easy to execute. Furthermore, the scalability of the reaction and the ability to derivatize the product were demonstrated to highlight the practicality of this approach.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Zhenni Zhao, Zhi Ou, Subarna Jyoti Kalita, Feng Cheng, Qian Huang, Yangyi Gu, Yuhao Wang, Yan Zhao, Yiyong Huang
Summary: This paper reports the first example of a stereoconvergent reaction involving 1,3-dipolar cycloaddition of nitrile oxides and nitrile imines with electron-deficient olefins. The reaction produces compounds with multiple stereogenic centers and exhibits excellent regio- and diastereoselectivities. Through control experiments and calculations, the possibility of thermodynamically stable diastereomers formation during the reaction is ruled out, and a stepwise mechanism is proposed.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Organic
Dennis Svatunek, Thomas Hansen, Kendall N. Houk, Trevor A. Hamlin
Summary: The Lewis base F- catalyzes the 1,3-dipolar cycloaddition between CO2 and nitrilimines by activating the nitrilimine and enhancing the rate of the reaction. The strength of primary orbital interactions between the reactants is the origin of this catalysis. The Lewis base activated nitrilimine-F- has high-lying filled FMOs, which promote a rapid nucleophilic attack and overall cycloaddition with CO2.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
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
Chemistry, Organic
Zhenjie Qi, Shaozhong Wang
Summary: A protocol was developed for the construction of cyclic nitrones using gold-catalyzed 1,3-azaprotio transfer of allenyloximes under photoirradiation. The photoisomerization of oximes could convert the inert stereoisomer to a reactive one. This photodriven and gold-catalyzed ring formation could also be applied to thermodynamically stable aryl ketoximes with an E-configuration.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Baofu Zhu, Wen Li, Haixin Chen, Minjian Wu, Jijing Hu, Hua Cao, Xiang Liu
Summary: A mechanochemical Cu-catalyzed [3 + 2] cycloaddition of azinium-N-imines with nitriles was reported under solventless grinding conditions. Various 1,2,4-triazolos derivatives were obtained in high yields. The developed protocol offers advantages in functional-group compatibility, scalability, and shorter reaction time.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Mohammed F. F. Radwan, Elghareeb E. E. Elboray, Hemat M. M. Dardeer, Yusuke Kobayashi, Takumi Furuta, Shohei Hamada, Toshifumi Dohi, Moustafa F. F. Aly
Summary: 1,3-Dipolar cycloaddition through in situ generation of azomethine ylide provides a straightforward and critically important sustainable approach for access to diverse pyrrolidine chemical space. Metal-free AcOH-activated 1,3-dipolar cycloaddition protocol was developed to synthesize uncommon pyrrolidine cycloadducts with excellent diastereoselectivity. The reaction mechanism and the key role of AcOH were supported by experimental, theoretical and spectroscopic studies.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Inorganic & Nuclear
Joseph Yount, Matthias Zeller, Edward F. C. Byrd, Davin G. Piercey
Summary: The novel energetic material DNDAABT was synthesized via mixed acid nitration of electrochemically generated TAABT, with various energetic salts also prepared and characterized. Despite predictions of low sensitivities, DNDAABT and its salts showed primary explosive sensitivities with relatively high thermal stabilities for primary N-nitramines.
INORGANIC CHEMISTRY
(2021)
