Article
Chemistry, Multidisciplinary
Yuki Yamamoto, Akiya Ogawa
Summary: The cycloaddition reaction of o-diisocyanoarenes with interelement compounds under light enables the synthesis of bisphosphinated quinoxalines through the radical cyclization pathway, elucidating the reaction mechanism and product selectivity. Additionally, the reaction of diphosphines with isocyanides having o-functional groups provides further insights into the bisphosphination process. Furthermore, the one-pot synthesis of Pd-II-quinoxaline complex is achieved through this developed reaction.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Organic
Hongbo Qi, Shuai Xu, Ruiguo Zhao, Shufeng Chen
Summary: A convenient and mild method for the synthesis of ynones via NIS-mediated oxidation of propargyl alcohols has been described. The reaction provides ynones with a variety of functional groups in moderate to excellent yields, and the flexibility of this method has been demonstrated through gram-scale experiment and further transformation.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Aline A. N. de Souza, Aloisio de A. Bartolomeu, Timothy J. Brocksom, Timothy Noel, Kleber T. de Oliveira
Summary: The electrochemical sulfenylation reaction was investigated in both batch and continuous flow regimes, with quaternary ammonium salts identified as the best mediators. The tolerance of Boc-cysteine to the reaction protocol was noted, increasing its relevance. The methodology was found to be scalable in both batch and continuous flow conditions, offering potential for further studies involving important functional groups in organic synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Daisy Sarma, Biju Majumdar, Barsha Deori, Siddarth Jain, Tridib K. Sarma
Summary: The study presents a catalyst-free photoinduced process for the synthesis of N-heterocyclic moieties in aqueous medium using TBHP as an oxidizing agent, driven by the enhanced rate of decomposition under visible light irradiation. This environmentally friendly pathway eliminates the need for metal catalysts or photocatalysts, offering a green and sustainable approach in organic synthesis.
Article
Chemistry, Applied
Jingyu Zhang, Wei Xia, Saskia Huda, Jas S. Ward, Kari Rissanen, Markus Albrecht
Summary: A copper(II)-catalyzed dearomative cyclization amination of N-(2-aminobenzoyl) indoles is described, yielding tetracyclic indolines under mild conditions with good yields. Tetracyclic 5a,6-dihydroindolo[2,1-b]quinazolin-12(5H)-ones are obtained in good to excellent yields (up to 99% yield) by N-Ts bond cleavage using trifluoromethanesulfonic acid (TfOH) mediation. The resulting compounds can be easily functionalized through simple synthetic methods.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Dong Zhang, Jinlin Cai, Jinze Du, Xujia Wang, Wei He, Zhao Yang, Chengkou Liu, Zheng Fang, Kai Guo
Summary: A green and practical electrochemical method has been developed for the synthesis of C-3-sulfonated benzothiophenes, achieving moderate to good yields of compounds with important functional groups. Mechanistic studies suggest a tandem radical addition-cyclization pathway, and the protocol is easy to scale up with good reaction efficiency.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Monica Donnola, Annalisa Airoldi, Alessandro Barozza, Jacopo Roletto, Paolo Paissoni
Summary: A process for the synthesis of lofexidine hydrochloride, an alpha 2-adrenergic receptor agonist used for treating opioid withdrawal, is presented, which is efficient, cost-effective, and easily scalable. The process involves a one-pot amidation/imidazoline ring formation reaction and allows for the efficient preparation of the desired product.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Article
Chemistry, Multidisciplinary
Hui Zheng, Ying Han, Jing Sun, Chao-Guo Yan
Summary: In summary, a convenient synthetic protocol for hexasubstituted benzene derivatives was successfully developed through DABCO-promoted domino reaction. The reaction mechanism involves sequential nucleophilic addition, Michael addition, annulation, and aromatization processes.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Applied
Zhenghui Liu, Shien Guo, Peng Wang, Zhenzhong Yan, Tiancheng Mu
Summary: A method for the synthesis of complicated quinoline derivatives via oxidative annulations using a rhodium catalytic system was proposed. Through systematic exploration and optimization of reaction parameters, 55 target molecules were obtained with moderate to high yields. The combination of double oxidants facilitated smooth conversion, and a clear reaction mechanism was elucidated. Upscaling experiments confirmed the practical applicability of the method.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Huai-Bo Zhao, Jin-Liang Zhuang, Hai-Chao Xu
Summary: An electrochemical method for the synthesis of benzimidazoles through dehydrogenative cyclization of N-aryl amidines is reported in this study. The reactions were conducted under simple constant current conditions in an undivided cell without the need for catalysts or chemical oxidants, producing H-2 as the only theoretical byproduct.
Article
Chemistry, Applied
Xin Yuan, Jie Liu, Long-Zhou Qin, Xiu Duan, Jian Wang, Meng-Yu Wu, Jiang-Kai Qiu, Kai Guo
Summary: This article reports a direct, visible-light-mediated, radical-cascade addition/sulfonylation/cyclization reaction with DABCO middot(SO2)2 and thianthrenium salts. The protocol provides an operationally-convenient access to various sulfonated functionalized indole [2,1-a] isoquinolines under mild conditions. This transformation features high functional-group tolerance, operational ease, and broad substrate scope. Preliminary studies suggest that the method proceeds through a radical pathway.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Ling Li, Zhen-Ting Liu, Xiang-Ping Hu
Summary: A copper-catalyzed one-pot cascade cyclization reaction has been developed for the synthesis of substituted isoindolo[2,1-a]quinoxalines from 2-(1-(acetyloxy)propargyl)benzaldehydes and o-phenylenediamines. The reaction shows high yields of 41-88% with readily available starting materials and simple operational procedure, indicating its broad substrate scopes.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Biochemistry & Molecular Biology
Abbas Amini, Azadeh Fallah, Ahmad Sedaghat, Ahmad Gholami, Chun Cheng, Anju R. Gupta
Summary: Natural phosphate and synthetic fluorapatite phosphate have been proposed as stable, inexpensive, readily available, and recyclable catalysts for the synthesis of quinoxaline at room temperature. Natural phosphate showed higher catalytic activity compared to synthetic fluorapatite phosphate, and the recycling process did not significantly impact the catalytic property of natural phosphate.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2021)
Article
Chemistry, Organic
Dan Liu, Xueyan Liu, Jing Sun, Chao-Guo Yan
Summary: The DABCO-promoted annulation reaction of bindone and different substrates showed unique molecular diversity under varying reaction conditions. The use of different substrates and solvents resulted in significant differences in the types of reaction products and yields.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Ariprasanth Ramalingam, Gopal Chandru Senadi
Summary: Here, we report a simple and straightforward magnetic heterogeneous catalytic approach using H2O as an environmentally friendly solvent to synthesize benzimidazole and quinoxaline scaffolds from o-phenylene diamines and primary amines. The method has the advantages of high yields and reusable catalyst, making it suitable for industrial synthesis.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
