Article
Chemistry, Organic
Luke R. Odell, Bobo Skillinghaug, Christof Matt, Peng Wu, Tobias Koolmeister, Matthieu Desroses, Sabin Llona-Minguez, Olov Wallner, Thomas Helleday, Martin Scobie
Summary: Here, we describe the development of a new cascade reaction for the synthesis of rare indazole acetic acid scaffolds. By heating 3-amino-3-(2-nitroaryl)propanoic acids with an appropriate nucleophile/solvent under basic conditions, three distinct indazole acetic acid derivatives (unsubstituted, hydroxy, and alkoxy) can be conveniently synthesized. The reaction can tolerate various functional groups and electronic effects, resulting in the synthesis and characterization of 23 novel indazole acetic acids. This work provides a valuable synthetic strategy for drug discovery programs.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Marc Devillard, Nour Nour Eddine, Marie Cordier, Gilles Alcaraz
Summary: A straightforward synthetic methodology for the preparation of photochromic siloles based on the dithienylethene motif has been developed. This method relies on an efficient palladium-catalyzed annulation reaction of a 2,3-bis(3-thienyl)-silirene with terminal alkynes in mild conditions. The reaction is functional group-tolerant and can be extended to the synthesis of photochromic polymers with different degrees of photochromic unit incorporation by adjusting the polymer/silirene stoichiometric ratio.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Applied
Yong-Xing Song, Da-Ming Du
Summary: The aza-Michael addition cascade reaction is an important synthetic method for constructing functionalized C-N bonds, widely used in the synthesis of chiral drugs, intermediates, and natural products. This review highlights recent developments in asymmetric synthesis, including various types of aza-Michael addition triggered cascade reactions, reaction mechanisms, and derivatization experiments.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Feng Zhang, Yujie Niu, Dacheng Hong, Yilin Ye, Yuhui Hua, Shihao Ding, Yandong Zhang
Summary: Atkamine, a complex marine alkaloid, poses a challenging synthesis task for chemists due to its intricate structure. This study presents a synthetic strategy to construct key intermediates of atkamine, including a [5+2] annulation and an asymmetric Michael addition. Successful synthesis of long-chain aliphatic aldehyde and chiral amino acetal fragments was achieved, leading to the construction of a simplified tetracyclic intermediate with the core structure of atkamine.
CHINESE CHEMICAL LETTERS
(2021)
Review
Chemistry, Organic
Barnali Jana, Monotosh Mondal, Shibashis Halder, Atanu Mahata, Sameer Saurav, Sushovan Paladhi
Summary: This article summarizes the progress made in the past 10 years in using unprotected and protected maleimides for asymmetric organocatalytic 1,4-conjugate additions. The review provides an overview of different types of nucleophiles, catalysts, substrate scope, limitations, mechanism, and synthetic utilities for each reaction. It encourages researchers worldwide to focus on the development of new methodologies, including asymmetric photo redox catalysis, for the further functionalization of maleimides.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Gurupada Hazra, Sayantan Kundu, Rambabu Dandela, Barla Thirupathi
Summary: A facile synthetic approach for 6H-pyrrolo[3,2,1-de]acridines has been developed by using a cascade N-nucleophilic addition-cyclic Michael addition process. The reaction was conducted under metal-free conditions using arynes and indoles substituted with Michael acceptors. Additionally, photophysical studies showed that the newly synthesized pyrroloacridine compounds exhibited good fluorescence emission properties.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jacob C. Hood, Yannick Tshikaya, Aaren R. Manz, Marcus C. LaPorte, Douglas A. Klumpp
Summary: In this study, a series of conjugate addition reactions were successfully performed using vinyl-substituted N-heterocycles in acid-catalyzed conversions, resulting in the formation of pyridyl and related heterocyclic products. The nucleophiles used in these reactions include 1,3-dicarbonyl compounds, cyano esters, cyano sulfone, and malonylnitrile, while the Michael accepting groups include vinyl-substituted pyridines, quinoline, and pyrazine. Double conjugate addition reactions were also achieved using 2,6-divinylpyridine and related systems.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yimin Hu, Wangyu Shi, Zhengyang Yan, Jianning Liao, Min Liu, Jiaqing Xu, Wei Wang, Yongjun Wu, Cheng Zhang, Hongchao Guo
Summary: An efficient method using K2CO3 catalysis has been developed for the 1,4-addition/intramolecular cyclization/aromatization reaction of aurone-derived 1-azadienes with trisubstituted allenoates, resulting in a series of benzofuro[3,2-b]pyridines in moderate to excellent yields. The reaction proceeds efficiently under an air atmosphere without the need for transition metal catalysts, providing a concise approach to benzofuro[3,2-b]pyridines.
Review
Biochemistry & Molecular Biology
Biswajit Panda, Gianluigi Albano
Summary: Nicotine, a chiral alkaloid found in tobacco plants, targets and stimulates nicotinic acetylcholine receptors, leading to interest in developing synthetic analogues. Current research focuses on synthesizing conformationally restricted analogues of nicotine using various catalytic processes. Biological studies on the activity of these analogues on specific nAChR subunits are also considered.
Article
Chemistry, Organic
Subaramaniam Thangamalar, Kannupal Srinivasan
Summary: The ring-opening reaction of nitro-substituted donor-acceptor cyclopropanes with pyrazoles in DMSO was investigated. Unexpectedly, the cyclopropanes underwent Kornblum-type ring-opening oxidation with DMSO to form aroylmethylidene malonates as intermediates in the reactions. The intermediates further underwent aza-Michael addition with pyrazoles in tandem manner to give the corresponding aza-Michael adducts. The highlights of the methodology include the occurrence of ring-opening/oxidation under neutral conditions with DMSO and formation of aza-Michael adducts with pyrazoles under catalyst-free conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Jie Wang, Shan-Shan Wang, Jun Xiao, Yu-Jie He, Xin-Yan Wu, Xingguang Li, Pei-Nian Liu
Summary: CF3-substituted imidoyl sulfoxonium ylides (TFISYs) are versatile and powerful synthons for the synthesis of diverse CF3-substituted N-heterocycles, offering broad application prospects.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Satyajit Roy, Sandip Kumar Das, Hillol Khatua, Subrata Das, Krishna Nand Singh, Buddhadeb Chattopadhyay
Summary: An iron-catalyzed denitrogenative rearrangement of 1,2,3,4-tetrazole has been developed, showcasing the synthesis of complex-N-heterocyclic products and a short synthesis of a bioactive molecule. This discovery emphasizes the progress of radical activation strategy, which is expected to find wide application in medicinal chemistry, drug discovery, and natural product synthesis research.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Bubul Das, Nikita Chakraborty, Kamal Krishna Rajbongshi, Bhisma K. Patel
Summary: This article reviews different methods and approaches for the synthesis of N/O/S-heterocycles using styrene as an annulating partner in the past five years. These heterocycles are widely present in the core structure of various natural products, pharmaceuticals, and agrochemicals.
Article
Chemistry, Organic
Davit Hayrapetyan, Valeriya Stepanova
Summary: In this study, spirocyclic pyrrolidones and piperidones were synthesized via [3+2]- and [3+3]-aza-annulation reactions starting from readily available alpha-ketolactones and alpha-ketolactams. The annulation reactions proceeded with good yields and excellent diastereoselectivity, creating one C-C and two C-N bonds, as well as three new stereocenters in a fast and efficient manner.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Xiaoxiang Zhang, Yingying Zhang, Xiaoting Gu, Zhuan Zhang, Wanxing Wei, Taoyuan Liang
Summary: A copper-mediated 2,3-difunctionalization of indoles to afford 3-halogenated 2,3 '-biindoles is described. The protocol uses readily available feedstocks and a naturally abundant copper catalyst system, which allows the regioselective formation of C-C and C-X (X = Cl & Br) bonds in one single operation. Copper metal salt serves not only as a catalyst but also as a reactant to provide the source of halogen, avoiding the use of environmentally unfriendly reagents and displaying good functional group compatibility.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
