Article
Chemistry, Organic
Diksha Rajput, Gowsia Jan, Muthu Karuppasamy, Nattamai Bhuvanesh, Subbiah Nagarajan, C. Uma Maheswari, J. Carlos Menendez, Vellaisamy Sridharan
Summary: An efficient cascade annulation reaction using secondary amine catalyst was developed for the synthesis of functionalized 2H-chromenes and 1,2-dihydroquinolines with a p-quinone methide scaffold. The microwave-assisted strategy achieved high yields and completion of reactions in just 15 min. The synthesized products were further transformed into valuable compounds via a palladium-catalyzed double C-H bond activation process and epoxidation.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Kai Li, Shengli Huang, Tianyu Liu, Shiqi Jia, Hailong Yan
Summary: We demonstrated an organocatalytic asymmetric dearomatizing hetero-Diels-Alder reaction of benzene derivatives, which allows the synthesis of diverse stereochemically complex compounds and oxahelicenes. The high complexity and three-dimensionality of the products are crucial for their potential applications in materials science and drug discovery.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Review
Chemistry, Physical
Mercedes Zurro, Aitor Maestro
Summary: This paper reviews the recent literature on the catalytic methodologies for the derivatization of aza-QM, including organocatalytic and organometallic approaches. The review analyzes various catalytic systems, involving chiral NHC carbenes, phosphoric acids, phosphoramidites, phosphine, copper, and palladium catalysis, showcasing their applicability for the synthesis of a diverse array of N-containing compounds, many of which exhibit biological activity.
Article
Chemistry, Multidisciplinary
Shaukat Ali, Muhammad Israr
Summary: This paper highlights the recent studies on the organocatalytic asymmetric dearomatization of nonactivated arenes, obtaining complex stereoisomeric products by harnessing the reactivity of chiral vinylidene ortho-quinone methides (VQMs) generated in situ.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Rupashri Dash, Sudhir Kumar Hota, Sandip Murarka
Summary: We describe an efficient higher order conjugate addition reaction of azauracils to substituted para-quinone methides (p-QMs) mediated by triethylamine, forming previously unknown diarylmethane scaffolds through C-N bond formation. This protocol offers mild conditions, high atom economy, broad scope, and allows convenient access to biologically relevant new chemical entities (NCEs) consisting of p-QM and azauracil hybrids in good to excellent yields.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Qinfang Yan, Yi Jiang, Xianheng Song, Guoqing Lu, Qianzhong Zhang, Zhibo Du, Albert S. C. Chan, Yong Zou
Summary: A facile and practical approach for the synthesis of natural coumestans and derivatives starting from 2',4'-dihydroxyl-3-arylcoumarins has been developed. The process involves a sequential intramolecular dehydrogenation/oxa-Michael reaction efficiently promoted by 1,8-diazabicyclo[5.4.0]undec-7-ene at 40 degrees C under metal- and ligand-free conditions with good functional group compatibility.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Pavit Kumar Ranga, Feroz Ahmad, Prashant Nager, Prabhat Singh Rana, Ramasamy Vijaya Anand
Summary: The catalytic application of bis(amino)cyclopropenium ion in conjugate addition reactions has been investigated, with the hydrogen atom on the cyclopropene ring acting as a hydrogen-bond donor catalyst. Experimental studies have verified that the C-H hydrogen in the cyclopropene ring is solely responsible for catalyzing these transformations, activating the carbonyl group of p-quinone methide through hydrogen bonding.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Jian-Qiang Zhao, Wen-Jie Wang, Shun Zhou, Qi-Lin Xiao, Xi-Sha Xue, Yan-Ping Zhang, Yong You, Zhen-Hua Wang, Wei-Cheng Yuan
Summary: An unprecedented N-alkylation of 3-nitroindoles with para-quinone methides was developed for the first time. Using potassium carbonate as the base, a wide range of structurally diverse N-diarylmethylindole derivatives were obtained with moderated to good yields via the protection group migration/aza-1,6-Michael addition sequences. The reaction process was also demonstrated by control experiments.
Article
Chemistry, Organic
Fangzhi Hu, Liang Wang, Peng Wang, Zhanshuai Ding, Yuzhuo Chen, Lubin Xu, Xiong-Li Liu, Shuai-Shuai Li
Summary: The controllable synthesis of spirooxindole-fused dibenzo[b,f]oxocines and chromans from oxindole-embedded four-atom synthons and dibrominated compounds has been achieved through [4 + 4] and [4 + 2] cyclization reactions respectively. Additionally, the indole-fused nine-membered oxa-heterocycles can be selectively accessed by the ring expansion of spirooxindole-fused dibenzo[b,f]oxocines through carbocation rearrangement.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Kavyashree Kuppayya Gond, Mahagundappa Rachappa Maddani
Summary: In this study, isochroman-1,4-diones and addition products were selectively synthesized through KOBu-Catalyzed addition of sulfonylphthalides to p-quinone methides. It is noteworthy that isochroman-1,4-diones were obtained via an unprecedented oxidative annulation pathway. The research highlights the broad substrate scope, high yields, shorter reaction time, and mild reaction conditions. Furthermore, some addition products can be transformed into functionalized heterocyclic molecules. Additionally, the scalability experiment demonstrates the practical feasibility of preparing isochroman-1,4-diones in larger scale reactions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Review
Chemistry, Applied
Zhibin Yue, Fang Fang, Yan Xia, Pengfei Li, Wenjun Li
Summary: Conjugate addition is a powerful method in organic synthesis for forming carbon-carbon and carbon-heteroatom bonds. Advances in asymmetric conjugate addition have been made with the development of asymmetric catalysis, but controlling selectivity becomes a challenge in extended conjugated systems.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Organic
Shi-Lu Zheng, Long Chen
Summary: 2H-chromenes, as an important type of oxygen heterocycles, are widely found in natural products, pharmaceutical agents, and biologically relevant molecules. The synthesis of such compounds mainly involves benzopyran ring formation and late-stage functionalization of the parent 2H-chromenes.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Applied
Deyuan Meng, Jing He, Woojin Yoon, Hoseop Yun, Jung Tae Han, Jaesook Yun
Summary: In this study, the catalytic 1,6-addition of chiral alkyl copper nucleophiles generated from borylalkenes and a copper-hydride catalyst was successfully conducted under mild conditions. The controlled chemo- and stereoselectivity played a crucial role in the reductive coupling process, resulting in efficient synthesis of asymmetric 1,6-adducts of p-quinone methides through multicomponent and catalytic tandem reactions.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Zhiguang Zhang, Xiaoyu Tan, Ao Sui, Bingzhu Zhang, Yong Zhang
Summary: A DBU-catalyzed 1,6-addition reaction of quinazolinones and quinolones with para-quinone methides under mild conditions is reported. Diarylmethane compounds functionalized with quinazolinones and quinolones were obtained in good yields (41-95%) with DBU as catalyst.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Hongmei Qin, Qimei Xie, Long He
Summary: This study developed a simple and convenient method to synthesize functionalized chroman-spirobenzofuran-2-one scaffolds via oxa-Michael/1,6-conjugated addition, providing an efficient strategy for constructing desired spirocyclic compounds.
Article
Chemistry, Organic
Junwei Wang, Lei Zhao, Quanjin Rong, Cheng Lv, Yu Lu, Xiang Pan, Lin Zhao, Lihong Hu
Article
Chemistry, Medicinal
Junwei Wang, Xiang Pan, Yi Song, Jian Liu, Fei Ma, Ping Wang, Yan Liu, Lin Zhao, Di Kang, Lihong Hu
Summary: Compound 17, a novel FLT3 inhibitor, demonstrated potent inhibitory activity and good selectivity against FLT3-ITD-positive AML, as well as strong inhibitory effects against associated acquired resistance mutations. In vivo studies showed that compound 17 significantly suppressed tumor growth without obvious toxicity, suggesting its potential as a promising drug candidate for treating FLT3-ITD-positive AML.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Organic
Junwei Wang, Lin Zhao, Caihong Li, Lei Zhao, Kun Zhao, Yang Hu, Lihong Hu
Summary: An efficient synthetic approach using iridium-catalyzed [4+3] cyclization has been developed successfully, providing valuable seven-membered heterocyclic frameworks with high yield (up to 97%) and diastereoselectivity (dr>20:1).
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Xiaolong Xie, Dandan Yuan, Ben Ma, Jiaming Jin, Enpeng Wang, Wenyi Zhou, Yaowen Hu, Lihong Hu, Junwei Wang
Summary: This study presents a controllable divergent synthesis method for heterocycles, allowing the synthesis of different ring sizes from the same starting materials. By controlling the reaction conditions, selective synthesis of products can be achieved, and the reaction mechanism has been investigated.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Medicinal
Qi Lv, Xiang Pan, Dan Wang, Quanjin Rong, Ben Ma, Xiaolong Xie, Yinan Zhang, Junwei Wang, Lihong Hu
Summary: Inhibiting tumor-associated macrophages by blocking CSF-1/CSF-1R signal has become a promising strategy for cancer immunotherapy. A novel series of orally highly effective CSF-1R inhibitors were designed, among which compound 21 showed excellent inhibitory activity and potent antiproliferative effects against colorectal cancer cells. Additionally, compound 21 demonstrated superior efficacy over PLX3397 in vivo, making it a promising candidate for colorectal cancer immunotherapy.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Di Kang, Xiang Pan, Yi Song, Yan Liu, Dan Wang, Xuejun Zhu, Junwei Wang, Lihong Hu
Summary: In this study, a series of water-soluble triptolide prodrugs were synthesized and evaluated for their release rate, pharmacokinetic characteristics, and anti-tumor effect. The results showed that TP-P1, a water-soluble prodrug, exhibited superior release rate and synthetic yield compared to Minnelide, a water-soluble triptolide prodrug currently in clinical trials. TP-P1 demonstrated effective tumor reduction and enhanced the efficacy of FLT3 inhibitors in treating AML.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Junwei Wang, Xiang Pan, Quanjin Rong, Lei Zhao, Lin Zhao, Weichen Dai, Kun Zhao, Lihong Hu
