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)
Review
Chemistry, Organic
Rida Noor, Ameer Fawad Zahoor, Syed Ali Raza Naqvi, Atta ul Haq, Rabia Akhtar
Summary: This review examines the synthetic routes attempted in the past two decades for forming large size carbocycles and heterocycles using ring expansion reactions, including lactams, boracycles, benzocycloheptenones, azaborinine, and azepine derivatives. Various rearrangement and cycloaddition reactions have been discussed.
SYNTHETIC COMMUNICATIONS
(2022)
Review
Chemistry, Organic
James Bowen, Luoyi Wang, Matthew P. Crump, Christine L. Willis
Summary: Tetrahydropyrans (THPs) are common structural motifs found in natural products and synthetic therapeutic molecules. They are often assembled via intramolecular reactions involving oxy-Michael additions or ring opening of epoxy-alcohols. The synthetic approaches for endo-selective intramolecular epoxide ring opening (IERO) of 4,5-epoxy-alcohols and their applications in natural product synthesis are outlined in this review. Additionally, the biosynthesis of THP-containing natural products utilizing IERO reactions is also discussed.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Zongli Xiong, Fuxing Xu, Yuqiao Zhou, Rong Zhang, Yulong Zhang, Yushuang Chen, Weijun Yao, Zhen Wang
Summary: An efficient and selective method for the [1,3] rearrangement of quinolin-2(1H)-ones has been developed using a chiral bisoxazoline/copper complex. The strategy allows for the synthesis of 1,4-dihydroquinoline-2,3-diones with a quaternary stereocenter and further cyclization to obtain optically active 3,4-dihydroquinolin-2-ones with broad substrate scope.
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, Multidisciplinary
Kseniya V. Belyaeva, Lina P. Nikitina, Veronika S. S. Gen, Ivan V. Saliy, Lyubov N. Sobenina, Andrei V. Afonin, Anton V. Kuzmin, Alexander V. Vashchenko, Boris A. Trofimov
Summary: Heterocyclic systems of benzo[1,4]diazocinone/pyrrole ensembles, which are pharmaceutically oriented and previously unknown, have been synthesized through a catalyst-free mild insertion reaction. This reaction expands the aromatic five-membered heterocyclic ring into a highly unsaturated eight-membered heterocyclic system, incorporating pyrrole-ringed structures. The proposed reaction mechanism involving dipole and ylide intermediates has been confirmed by quantum chemical calculations (DFT).
Article
Chemistry, Organic
Yanfeng Gao, Hui Wang, Xiaoquan Chen, Yiyang Qiao, Zhiwei Miao
Summary: We present a highly efficient and diastereoselective gold and palladium sequential relay catalysis system for the synthesis of furan-fused eight-membered heterocycles. By utilizing a one-pot procedure, readily available enynamides undergo cyclization to generate azadienes in situ, which then engage in diastereoselective formal[4 + 4] cycloadditions with gamma-methylene-delta-valerolactones. This method enables the rapid and efficient construction of a range of furan-fused azacyclooctanes with diverse substituents in good yields (63-97%) and a high level of diastereoselectivity (7:1 → 20:1 dr).
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Maximilian P. Mueller, Alexander Hinz
Summary: Silacycles are widely used building blocks in organic synthesis. In this study, small silacycles were expanded catalytically to form larger cyclic compounds. The reactivity and reaction mechanisms of these silacycles were investigated, showing that they can undergo ring expansion reactions and subsequent isomerization reactions. This research provides insights into the reactivity patterns of silacycles and their potential applications.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Malte Leverenz, Guillaume Masson, Domingo Gomez Pardo, Janine Cossy
Summary: Alpha-trifluoromethyl azocanes were synthesized efficiently from 2-(trifluoropropan-2-ol) piperidines via metal-free ring-expansion with a bicyclic azetidinium intermediate. The opening of the azetidinium intermediate was achieved with various nucleophiles in excellent regio-, diastereo- and enantioselectivity and good yields. The relative configuration of the piperidines and azocanes was determined, providing opportunities for further derivatization of the deprotected azocanes.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Multidisciplinary Sciences
Julia C. Reisenbauer, Ori Green, Allegra Franchino, Patrick Finkelstein, Bill Morandi
Summary: Reliable strategies for directly editing the core skeleton of pharmaceutical lead compounds are still scarce despite recent developments in the field. This study presents a method for skeletal editing of indoles through nitrogen atom insertion, demonstrating its utility in late-stage skeletal editing of several commercial drugs.
Review
Chemistry, Organic
Navjeet Kaur, Neha Ahlawat, Yamini Verma, Pooja Grewal, Pranshu Bhardwaj, Nirmala Kumari Jangid
Summary: Metal-mediated formation of heterocycles is an emerging and important strategy in organic chemistry. Silver-assisted cyclic reactions are highly efficient for the synthesis of five-membered fused N-heterocyclic compounds. This review article covers the applications of silver in the preparation of these compounds.
CURRENT ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Peter Wonneberger, Nils Koenig, Menyhart B. Sarosi, Evamarie Hey-Hawkins
Summary: Reduction of 1-phospha-2-azanorbornene derivative leads to formation of a novel compound 1-phosphabicyclo[3.2.1]octa-2,5-diene and an unusual 2H-phosphole dimer. Additionally, 3H-phospholes were found to potentially act as dienophile in the dimerisation reaction under elevated temperatures, contrary to previous assumptions of their synthetic irrelevance.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Applied
Fernando Martinez-Lara, Anisley Suarez, Noelia Velasco, Samuel Suarez-Pantiga, Roberto Sanz
Summary: The gold-catalyzed transformation of propargylic glycols with thiols results in the formation of alpha-indol-3-yl alpha-((Z)-2-thioalkenyl) ketones through a complex but selective reaction mechanism. This sequence involves regioselective thiolation of indolyl diols followed by the attack of sulfur on the activated alkyne, rather than the indole. The final compounds are obtained in high yields from simple starting materials such as indolyl acyloins, ethynyl magnesium bromide, and thiols.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Miguel A. Munoz-Torres, Fernando Martinez-Lara, Marta Solas, Samuel Suarez-Pantiga, Roberto Sanz
Summary: The combination of organolithium chemistry with gold catalysis offers a new synthetic strategy for accessing polysubstituted indoles and carbazoles. This method utilizes ketopyrroles as starting materials and involves a series of reactions to selectively synthesize the desired products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Applied
Dimitris Matiadis
Summary: 2-Pyrazolines are important five-membered heterocycles with two adjacent nitrogen atoms. They have various functional groups and unique biological properties, and are used as building blocks. In recent years, there has been significant progress in the synthesis of 2-pyrazolines, with the development of novel strategies and improvements of existing protocols. This review summarizes the synthetic methodologies from 2012 to 2022, discussing the challenges, capabilities, scopes, and limitations of the reactions, as well as substitution patterns and mechanisms where applicable.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Dewi Susanti, Li-Juan Liu, Weidong Rao, Sheng Lin, Dik-Lung Ma, Chung-Hang Leung, Philip Wai Hong Chan
CHEMISTRY-A EUROPEAN JOURNAL
(2015)
Review
Chemistry, Organic
Xiaoxiang Zhang, Xiaoping Sun, Jihuai Tan, Hui Fan, Weidong Rao
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Organic
Xiaoxiang Zhang, Xiaoping Sun, Weidong Rao
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Multidisciplinary
Weidong Rao, Dewi Susanti, Benjamin James Ayers, Philip Wai Hong Chan
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2015)
Article
Chemistry, Multidisciplinary
Xiaoxiang Zhang, Xiaoping Sun, Hui Fan, Chang Lyu, Ping Li, Haifei Zhang, Weidong Rao
Article
Chemistry, Organic
Xiaoxiang Zhang, Ping Li, Chang Lyu, Wanxiong Yong, Jing Li, Xinbao Zhu, Weidong Rao
ORGANIC & BIOMOLECULAR CHEMISTRY
(2017)
Article
Chemistry, Multidisciplinary
Weidong Rao, Philip Wai Hong Chan
CHEMISTRY-A EUROPEAN JOURNAL
(2014)
Article
Chemistry, Multidisciplinary
Weidong Rao, Sally, Stuart Neil Berry, Philip Wai Hong Chan
CHEMISTRY-A EUROPEAN JOURNAL
(2014)
Article
Chemistry, Organic
Wan Teng Teo, Weidong Rao, Ming Joo Koh, Philip Wai Hong Chan
JOURNAL OF ORGANIC CHEMISTRY
(2013)
Article
Chemistry, Organic
Weidong Rao, Sally, Ming Joo Koh, Philip Wai Hong Chan
JOURNAL OF ORGANIC CHEMISTRY
(2013)
Article
Chemistry, Multidisciplinary
Weidong Rao, Ming Joo Koh, Prasath Kothandaraman, Philip Wai Hong Chan
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2012)
Article
Chemistry, Multidisciplinary
Weidong Rao, Ming Joo Koh, Dan Li, Hajime Hirao, Philip Wai Hong Chan
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2013)
Article
Chemistry, Organic
Wan Teng Teo, Weidong Rao, Charmaine Jia Huan Ng, Shaun Wei Yong Koh, Philip Wai Hong Chan
Article
Chemistry, Organic
Ella Min Ling Sze, Ming Joo Koh, Yen Min Tjia, Weidong Rao, Philip Wai Hong Chan
Article
Chemistry, Organic
Jian Rui, Qi Zhang, Xin Wang, Xu Xu, Haijun Xu, Weidong Rao, Shifa Wang
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2017)