Review
Chemistry, Applied
Dong Wang, Laurent Desaubry, Gaoyu Li, Mindong Huang, Shixin Zheng
Summary: Recent progress has been made in the direct C-H functionalization of azines, but limitations still exist. In contrast, C2-functionalized pyridines and quinolines can be easily synthesized under appropriate activation conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Applied
Atsushi Umehara, Soma Shimizu, Makoto Sasaki
Summary: This report presents a general method for the direct N-acylation of N-heterocycles using the DMAPO/Boc(2)O system. This one-pot method allows for the synthesis of bulky N-acyl heterocycles from less nucleophilic N-heterocycles and sterically hindered carboxylic acids. The protocol has also been successfully applied to the one-pot N-acylation of 7-azaindoles.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Silvia Gonzalez-Pelayo, Olaya Bernardo, Javier Borge, Luis A. Lopez
Summary: The Lewis (or Bronsted) acid-catalyzed reaction of 2-aryl-N-sulfonyl aziridines with ferrocene and ruthenocene leads to the synthesis of new amino-functionalized metallocene derivatives through a regioselective ring opening of the aziridine. These functionalized metallocene derivatives can be used as precursors for the stereoselective synthesis of metallocene analogues of tetrahydroisoquinoline motif by a Pictet-Spengler type reaction. Additionally, isoquinoline analogues can also be accessed through a TfOH-catalyzed three-component reaction involving 2-aryl-N-sulfonyl aziridines, ferrocene (or ruthenocene), and formaldehyde.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Huan Luo, Junzhi Liu
Summary: Researchers developed a facile and effective method to synthesize a series of nitrogen-doped nanographenes in acceptable yields. Modification of the heptagonal ring endowed the resultant nanographenes with tunable physicochemical properties. Moreover, novel nanographenes containing nitrogen-doped pentagon-octagon pairs were obtained using the same synthetic strategy, demonstrating the superior versatility and efficiency of the proposed ring expansion method.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Tobias Wagener, Marco Pierau, Arne Heusler, Frank Glorius
Summary: In this study, a one-pot protocol for the synthesis of octahydroindoles, decahydroquinolines, and octahydroindolizines through a cascade reaction is presented.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Qi Zhang, Chunlin He, Siping Pang
Summary: A novel synthesis method for heterocyclic fused pyridazine di-N-oxides (triazole, furoxan, furazan) was described. The use of PIDA as a mild oxidant allowed for efficient synthesis of these motifs, solving the issues of harsh conditions and cumbersome manipulation in existing methods. Furthermore, the first synthesis of triazole fused pyridazine di-N-oxide provides a valuable building block for the preparation of biologically relevant molecules and energetic compounds.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Zhuotao Tan, Xiaowang Zhang, Mengjiao Xu, Yaping Fu, Wei Zhuang, Ming Li, Xiaojin Wu, Hanjie Ying, Pingkai Ouyang, Chenjie Zhu
Summary: Considerable progress has been made recently in developing chemoenzymatic processes by integrating the environmentally friendly features of biocatalysis with the versatile reactivity of chemocatalysis. This study reports a previously unexplored cooperative chemoenzymatic system for synthesizing N-heterocycles, which demonstrates high yields and provides a green and sustainable alternative.
Article
Chemistry, Physical
Atsushi Umehara, Soma Shimizu, Makoto Sasaki
Summary: This report presents a practical and operationally simple method for the direct N-acylation of less nucleophilic heterocycles and amides with carboxylic acids. The method utilizes the DMAPO/Boc(2)O system and does not require pre-activation of substrates. It demonstrates high yield, excellent functional group tolerance, and broad substrate scope, making it suitable for both academic and industrial laboratories.
Article
Chemistry, Organic
Jeong Kyun Im, Ilju Jeong, ByeongDo Yang, Hyeon Moon, Jun-Ho Choi, Won-jin Chung
Summary: An unprecedented N-chlorinative ring contraction reaction of 1,2-diazines was discovered and investigated, showing unique reactivity towards 1,4-dimethoxyphthalazine scaffold and TCICA. The assisting role of n-Bu4NCl and the use of a labile O-silyl group were identified to improve overall efficiency.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Johannes Winter, Tobias Prenzel, Tom Wirtanen, Dieter Schollmeyer, Siegfried R. R. Waldvogel
Summary: The use of electric current provides a sustainable and efficient method for the synthesis of quinoline N-oxides from readily available nitro compounds. The reaction employs mild and reagent-free conditions, and uses a simple undivided electrolysis cell with constant current set-up, leading to high conversion and atom economy. The synthesis of 30 differently substituted quinoline N-oxides was successfully achieved in up to 90% yield. Mechanistic insights were obtained through cyclic voltammetry studies, and the technical relevance of the reaction was demonstrated through a 50-fold scale-up.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
D. A. Chaplygin, A. A. Larin, L. L. Fershtat
Summary: An efficient synthesis method for N- and S-substituted arylglyoximes via one-pot transformations of available monoarylfuroxans was developed. The proposed approach involves furoxan ring cleavage followed by the generation of alpha-oximinoacetonitrile oxides which further react with N- and S-nucleophiles.
RUSSIAN CHEMICAL BULLETIN
(2022)
Article
Multidisciplinary Sciences
Jisoo Woo, Alec H. Christian, Samantha A. Burgess, Yuan Jiang, Umar Faruk Mansoor, Mark D. Levin
Summary: Discovery chemists use an iterative structural optimization method to identify purpose-tailored molecules, but the preparation of each candidate rarely matches their thought process. We report a method that allows chemists to directly switch between chemically distinct heteroaromatic scaffolds, addressing part of this problem.
Article
Chemistry, Organic
Tianyu Zhang, Han Zhuang, Luning Tang, Zhengyu Han, Wengang Guo, Hai Huang, Jianwei Sun
Summary: A novel intramolecular C-C formation process based on catalytic asymmetric oxetane opening by carbon nucleophiles has been developed, allowing for the rapid synthesis of valuable enantioenriched 2,3-dihydrobenzo[b]oxepines under mild conditions with good chemical efficiency and enantioselectivity. The products also serve as useful precursors to other valuable structures.
Article
Chemistry, Organic
Cormac Bracken, Marcus Baumann
Summary: Researchers have developed a continuous photochemical process that allows for the efficient synthesis of ketenimines via skeletal rearrangement of trisubstituted isoxazoles. This method provides a straightforward entry into these versatile building blocks, which were previously only observed spectroscopically. The application of this methodology is demonstrated by the transformation of isoxazoles into pharmaceutically relevant pyrazoles via isolable ketenimines.
Article
Chemistry, Organic
Yanyang He, Xiaowen Qin, Xinxu He, Xiao-Feng Wu, Zhiping Yin
Summary: An efficient intramolecular halo-amination reaction of unactivated alkenes for the synthesis of various halogenated N-heterocycles was developed via electrochemical anodic oxidation. This method allows the construction of a wide range of halogenated N-heterocycles at moderate to good yields, including three-, five-, and six-membered N-heterocycles, without the need for external oxidants and strong bases, representing an environmentally benign approach.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jack D. Bracken, Andrew D. Carlson, James H. Frederich, Mai Nguyen, Gordon C. Shore, Patrick G. Harran
TETRAHEDRON LETTERS
(2015)
Article
Chemistry, Organic
Jeffrey S. Cannon, James H. Frederich, Larry E. Overman
JOURNAL OF ORGANIC CHEMISTRY
(2012)
Article
Chemistry, Multidisciplinary
James H. Frederich, Patrick G. Harran
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2013)
Article
Chemistry, Organic
James H. Frederich, Jennifer K. Matsui, Randy O. Chang, Patrick G. Harran
TETRAHEDRON LETTERS
(2013)
