作者机构:
[Yi, Yun-Ying; Liu, Yu-Ting; Song, Ying-Chun; Wang, Ming-Xuan; Zhang, Wen-Xin; Wang, Zi-Yue; Zhu, Yan-Ping; Sun, Yuan-Yuan] Yantai Univ, Minist Educ, Collaborat Innovat Ctr Adv Drug Delivery Syst & Bi, Sch Pharm,Key Lab Mol Pharmacol & Drug Evaluat, Yantai 264005, Shandong, Peoples R China.;[Wu, An-Xin] Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Peoples R China.
通讯机构:
[Wu, AX ] C;[Zhu, YP ] Y;Yantai Univ, Minist Educ, Collaborat Innovat Ctr Adv Drug Delivery Syst & Bi, Sch Pharm,Key Lab Mol Pharmacol & Drug Evaluat, Yantai 264005, Shandong, Peoples R China.;Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Peoples R China.
关键词:
Total synthesis;Oxidative cyclization;Natural products;Switchable synthesis;Luotonin alkaloids
摘要:
A total synthesis strategy was developed for the synthesis of luotonin A, B and their analogues using synergistic FeCl3/KI-catalyzed oxidative cyclization. This protocol utilizes cheap and widely available N-propargyl 2-methyl-quinazolinones and arylamines under mild conditions, and it has a wide substrate scope and high atom economy. Different natural products (luotonin A, B and derivatives) can be synthesized via a unique switchable approach. Further transformations from luotonin B to luotonin E and structural modification of natural products demonstrate the potential applications of this method. Moreover, camptothecin can also be modified with the reported protocol to afford the hydroxyl-substituted product.
期刊:
JOURNAL OF ORGANIC CHEMISTRY,2024年89(6):3941-3953 ISSN:0022-3263
通讯作者:
Wang, JG;Wu, AX
作者机构:
[Wang, Jun-Gang; Ma, Lin-Lin] Guizhou Minzu Univ, Sch Chem Engn, Guiyang 550025, Guizhou, Peoples R China.;[Wang, Zheng-Hao; Tang, Yong-Xing; Wu, An-Xin; Zhou, You; Chen, Ting; Wu, Yan-Dong] Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Peoples R China.
通讯机构:
[Wu, AX ] C;[Wang, JG ] G;Guizhou Minzu Univ, Sch Chem Engn, Guiyang 550025, Guizhou, Peoples R China.;Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Peoples R China.
摘要:
An efficient synthetic method for constructing 2,3- and 2,4-disubstituted pyrimidio[1,2-b]indazole skeletons through I(2)-DMSO-mediated and substrate-controlled regioselective [4 + 2] cyclization is reported. The reaction conditions are mild, its operation is simple, and the substrate scope is wide. More than 60 pyrimidio[1,2-b]indazole derivatives have been synthesized, providing a new methodology for constructing related molecules and potentially enriching bioactive-molecule libraries.
期刊:
JOURNAL OF ORGANIC CHEMISTRY,2024年89(4):2505-2515 ISSN:0022-3263
通讯作者:
Wu, AX
作者机构:
[Wang, Can; Zhao, Peng] Taizhou Univ, Sch Pharmaceut Sci, Inst Adv Studies, Taizhou 318000, Zhejiang, Peoples R China.;[Wu, An-Xin; Zhou, You; Zhao, Peng] Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Peoples R China.
通讯机构:
[Wu, AX ] C;Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Peoples R China.
摘要:
A novel iodine-promoted difunctionalization of alpha-C sites in enaminones was demonstrated as a means of synthesizing a variety of fully substituted thiazoles by constructing C-C(CO), C-S, and C-N bonds. This transformation allows the realization of enaminones as unusual aryl C2 synthons and simultaneously allows the thioylation and dicarbonylation of alpha-C sites. A preliminary mechanistic study was performed and indicated that the cleavage of C=C bonds in enaminones involves a bicyclization/ring-opening and oxidative coupling sequence.
作者机构:
[Wang, Huai-Yu; Wu, Yan-Dong; Wu, An-Xin; Wu, Chun-Yan; Yu, Zhi-Cheng; Chen, Xiang-Long; Yang, Dong-Sheng] Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Hubei, Peoples R China.;[Tang, Bo-Cheng] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, State Key Lab Chem Biol & Drug Discovery, Kowloon, Hong Kong, Peoples R China.;[Li, Anling] Wuhan Univ, Ctr Gene Diag, Dept Clin Lab, Zhongnan Hosp, Wuhan 430062, Hubei, Peoples R China.;[Li, Anling] Wuhan Univ, Program Clin Lab Med, Zhongnan Hosp, Wuhan 430062, Hubei, Peoples R China.
通讯机构:
[Li, AL ] W;[Wu, YD; Wu, AX ] C;Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Hubei, Peoples R China.;Wuhan Univ, Ctr Gene Diag, Dept Clin Lab, Zhongnan Hosp, Wuhan 430062, Hubei, Peoples R China.;Wuhan Univ, Program Clin Lab Med, Zhongnan Hosp, Wuhan 430062, Hubei, Peoples R China.
关键词:
Defluoroarylation;Transition metal free;gem-Difluoroalkenes;Rongalite;Single electron transfer;C-C coupling;Redox reactions;Cross-coupling
摘要:
A transition‐metal‐free allylic defluorination reductive cross‐coupling between CF3‐alkenes and diaryliodonium salts mediated by rongalite has been described for the first time. This procedure was compatible with both linear and cyclic diaryliodonium salts, enabling a wide variety of substrates. The utility of this approach was demonstrated through gram‐scale synthesis and efficient late‐stage functionalizations of anti‐inflammatory drugs. Comprehensive Summary The conversion of CF3‐alkenes to gem‐difluoroalkenes using reductive cross‐coupling strategy has received much attention in recent years, however, the use of green and readily available reducing salt to mediate these reactions remains to be explored. In this work, a concise construction of gem‐difluoroalkenes, which requires neither a catalyst nor a metal reducing agent, was established. Rongalite, a safe and inexpensive industrial product, was employed as both a radical initiator and reductant. This procedure was compatible with both linear and cyclic diaryliodonium salts, enabling a wide variety of substrates (>70 examples). The utility of this approach was demonstrated through gram‐scale synthesis and efficient late‐stage functionalizations of anti‐inflammatory drugs.
作者机构:
[Wang, Huai-Yu; Ma, Jin-Tian; Wu, An-Xin; Wu, Chun-Yan; Zhuang, Shi-Yi; Yu, Zhi-Cheng; Wu, Yan-Dong; Chen, Xiang-Long; Yang, Dong-Sheng] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.;[Tang, Bo-Cheng] Hong Kong Polytech, Dept Appl Biol & Chem Technol, State Key Lab Chem Biol & Drug Discovery, Kowloon, Hong Kong 999077, Peoples R China.
通讯机构:
[Yan-Dong Wu; An-Xin Wu] K;Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. China
摘要:
A concise and efficient hydrodefluorination process was developed for the synthesis of gem-difluoroalkenes. This reaction employs rongalite as a masked proton source and does not require any additional catalysts or reductants. Notably, trifluoromethyl alkenes having both terminal and internal double bonds are compatible with this process, allowing for a wider range of substrates. The successful late-stage functionalizations of pharmaceuticals and gram-scale syntheses were used to demonstrate the viability of this method.
作者机构:
[Lei, Shuang-Gui; Wu, An-Xin; Zhou, You; Chen, Ting; Yu, Zhi-Cheng; Wu, Yan-Dong; Wang, Li-Sheng] Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Peoples R China.;[Gao, Meng] South China Univ Technol, Natl Engn Res Ctr Tissue Restorat & Reconstruct, Sch Mat Sci & Engn, Key Lab Biomed Mat & Engn,Minist Educ, Guangzhou 510006, Peoples R China.
通讯机构:
[Wu, AX ] C;[Gao, M ] S;Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Peoples R China.;South China Univ Technol, Natl Engn Res Ctr Tissue Restorat & Reconstruct, Sch Mat Sci & Engn, Key Lab Biomed Mat & Engn,Minist Educ, Guangzhou 510006, Peoples R China.
摘要:
An unprecedented dual alpha,beta-C(sp(2))-H functionalization/bicyclization strategy of o-hydroxyphenyl enaminones for the preparation of chromeno[2,3-b]pyrrol-4(1H)-ones has been established. The multi-component cascade reaction achieves dual alpha,beta-C(sp(2))-H functionalization of o-hydroxyphenyl enaminones to construct C2,C3-disubstituted chromenes for the first time, along with intramolecular cascade cyclization between two functional groups to construct four new bonds and two rings in one pot. Moreover, the products have polarity sensitivity and feature aggregation-induced emission (AIE) characteristics after simple modifications, which is promising for bioimaging and theranostic applications.
通讯机构:
[Xiang, Jia-Chen] S;[Ma, Jin-Tian] K;School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, China<&wdkj&>Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. China
摘要:
We herein report an efficient synthesis of 2-aroyl-3-arylquinolines from phenylalanines and anilines. The mechanism involves I(2)-mediated Strecker degradation enabled catabolism and reconstruction of amino acids and a cascade aniline-assisted annulation. Both DMSO and water act as oxygen sources in this convenient protocol.
作者机构:
[Liu, Rui; Xiang, Jia-Chen; Liao, Zhixin; Yuan, Peng; Zhu, Hui-Min] Southeast Univ, Sch Chem & Chem Engn, Nanjing 211189, Peoples R China.;[Wu, An-Xin] Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Peoples R China.;[Xiang, JC] Southeast Univ, Sch Chem & Chem Engn, Nanjing 211189, Peoples R China.;[Wu, An-Xin] Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Peoples R China.
通讯机构:
[Xiang, JC ; Wu, AX ] ;Southeast Univ, Sch Chem & Chem Engn, Nanjing 211189, Peoples R China.;Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Peoples R China.
摘要:
The precise aromatization of the C-ring of podophyllotoxone to access value-added dehydropodophyllotoxin derivatives conventionally requires the use of equivalent amounts of unsustainable oxidants and suffers from inefficiencies. Taking advantage of the hydridic character of the C8 and C8' of podophyllotoxone, we have developed an I(2)-DMSO catalytic manifold that enables a green and selective dehydrogenative aromatization to overcome these synthetic challenges. An unprecedented dehydrogenative amination of podophyllotoxone derivatives was also realized using aniline as the reaction partner.
作者机构:
[Wang, Huai-Yu; Chen, Xiang-Long; Wu, An-Xin; Chen, Ting; Wu, Chun-Yan; Yang, Dong-Sheng] Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Peoples R China.
通讯机构:
[Chen, XL; Wu, AX ] C;Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Peoples R China.
摘要:
Herein, we disclose a straightforward approach to access transition-metal-free reductive N-formylation of nitroarenes. This reaction integrates the dual role of rongalite, which acts as a reductant and a C1 building block concurrently. This provides an alternative method for the synthesis of N-aryl formamides from nitroarenes, including the construction of a C-N bond. The utility of this protocol was demonstrated by scale-up synthesis and late-stage functionalizations of complex molecules.
通讯机构:
[Wu, AX ] C;[Geng, X ] T;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.;Taizhou Univ, Adv Res Inst, Taizhou 318000, Zhejiang, Peoples R China.;Taizhou Univ, Sch Pharmaceut Sci, Taizhou 318000, Zhejiang, Peoples R China.
摘要:
A transition metal and external fluorine anion-free method has been developed for the efficient trifluoromethylation of sulfoxonium ylides with BrCF2CO2Et to afford alpha-trifluoromethyl ketones. Mechanistic investigation revealed that taking advantage of the dual role of BrCF2CO2Et, which concurrently acts as a CF2 and F source, is key to realizing this reaction. This method is applicable to the late-stage modification of biologically active compounds and can be readily scaled up.
作者机构:
[Tang, Yong-Xing; Wu, An-Xin; Zhou, You; Zhuang, Shi-Yi; Wu, Yan-Dong; Liu, Jin-Yi; Wang, Li-Sheng] Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Peoples R China.
通讯机构:
[Wu, AX ] C;Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Peoples R China.
摘要:
An I-2-DMSO mediated one-pot approach to imidazo[2,1-a]isoquinoline derivatives from readily available aryl methyl ketones and isoquinolin-1-amine has been demonstrated. This triple in situ cross-trapping strategy realizes the convergent integration of one self-sorting domino sequence with two linear domino sequences, efficiently generating multiple C-C/C-N/C-S/C-I bonds, along with a new imidazole ring and one quaternary carbon center. Furthermore, the iodo group and methylthio group of the product can undergo further transformations through coupling or oxidation reactions, demonstrating the utility of this method in synthetic chemistry.
通讯机构:
[Xiang, JC ] S;[Wu, AX ] C;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.;Southeast Univ, Sch Chem & Chem Engn, Nanjing 211189, Peoples R China.
摘要:
Concise synthesis of functionalized quinolines has received continuous research attention owing to the biological importance and synthetic potential of bicyclic N-heterocycles. However, synthetic routes to the 2,4-unsubstituted alkyl quinoline-3-carboxylate scaffold, which is an important motif in drug design, remain surprisingly limited, with modular protocols that proceed from readily available materials being even more so. We herein report an acidic I2–DMSO system that converts readily available aspartates and anilines into alkyl quinoline-3-carboxylate. This method can be extended to a straightforward synthesis of 3-arylquinolines by simply replacing the aspartates with phenylalanines. Mechanistic studies revealed that DMSO was activated by HI via a Pummerer reaction to provide the C1 synthon, while the amino acid catabolized to the C2 synthon through I2-mediated Strecker degradation. A formal [3 + 2 + 1] annulation of these two concurrently generated synthons with aniline was responsible for the selective formation of the quinoline core. The synthetic utility of this protocol was illustrated by the efficient synthesis of human 5-HT4 receptor ligand. Moreover, an unprecedented chemoselective synthesis of 2-deuterated, 3-substituted quinoline, featuring this reaction, has been established.
作者机构:
[Lei, Shuang-Gui; Wu, An-Xin; Ma, Jin-Tian; Zhou, You; Chen, Ting; Yu, Zhi-Cheng; Wu, Yan-Dong; Chen, Xiang-Long] Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Peoples R China.;[Xiang, Jia-Chen; Xiang, JC] Southeast Univ, Sch Chem & Chem Engn, Nanjing 211189, Peoples R China.
通讯机构:
[Xiang, JC ] S;[Wu, AX ] C;Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Peoples R China.;Southeast Univ, Sch Chem & Chem Engn, Nanjing 211189, Peoples R China.
摘要:
The pyrazolo-azepino-centred polyheterocyclic fused system is a privileged scaffold, but it lacks an effective synthetic approach, with modular synthesis being even more scarce. Accordingly, we herein report a highly efficient I-2-DMSO-mediated one-pot, four-component protocol to construct this fascinating scaffold. This system provides an unprecedented temperature-controlled highly selective formation of aromatics and non-aromatics, affording planar and non-planar tetracyclic architectures that can be interconverted surprisingly by simple methods. Mechanistically, a cooperative aza-[4 + 3] cycloaddition is responsible for the skeleton construction process, while the endogenous oxidant I-2 is responsible for the subsequential aromatization stage.
期刊:
JOURNAL OF ORGANIC CHEMISTRY,2023年88(16):12000-12012 ISSN:0022-3263
通讯作者:
Wu, AX;Zheng, KL
作者机构:
[Tang, Yong-Xing; Zhou, You; Wu, An-Xin; Zhuang, Shi-Yi; Wu, Yan-Dong; Liu, Jin-Yi; Chen, Xiang-Long] Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Peoples R China.;[Zheng, Kai-Lu] Guangdong Med Univ, Dongguan Affiliated Hosp 1, Guangdong Prov Key Lab Res & Dev Nat Drugs, Dongguan 523808, Peoples R China.;[Zheng, Kai-Lu] Guangdong Med Univ, Sch Pharm, Dongguan 523808, Peoples R China.;[Wu, An-Xin] Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Peoples R China.;[Zheng, Kai-Lu] Guangdong Med Univ, Dongguan Affiliated Hosp 1, Guangdong Prov Key Lab Res & Dev Nat Drugs, Dongguan 523808, Peoples R China.
通讯机构:
[Wu, AX ; Zheng, KL ] ;Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Peoples R China.;Guangdong Med Univ, Dongguan Affiliated Hosp 1, Guangdong Prov Key Lab Res & Dev Nat Drugs, Dongguan 523808, Peoples R China.;Guangdong Med Univ, Sch Pharm, Dongguan 523808, Peoples R China.
摘要:
An I(2)-DMSO-mediated multicomponent [3+1+2] cascade annulation reaction using aryl methyl ketones, enaminones, and benzo[d]isoxazol-3-amine as substrates has been developed. This metal-free reaction involved the transannulation of benzo[d]isoxazol-3-amines with the formation of two C-N bonds and a C-C bond in one pot. Notably, a pyrimidine ring with a 1,4-dicarbonyl scaffold could efficiently transform into a pyrimido[4,5-d]pyridazine skeleton. The phenolic hydroxyl group of the target product could undergo further modification with pharmaceuticals, demonstrating the utility of this method.
通讯机构:
[Wu, AX ] C;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
摘要:
A [3 + 1 + 2] cyclization–rearrangement reaction scheme was developed to synthesize pyrimido[1,2-b]indazoles from aryl methyl ketones, 3-aminoindazoles, and gem-diarylethenes. This metal-free process proceeds via a sequential aza-Diels–Alder reaction and Wagner–Meerwein rearrangement, and a possible reaction mechanism was demonstrated based on control experiments. This method exhibits good substrate compatibility and allows simple reaction conditions. Moreover, the products display significant aggregation-induced emission characteristics after simple modifications.
作者机构:
[Tang, Yong-Xing; Lei, Shuang-Gui; Wu, An-Xin; Zhou, You; Yu, Zhi-Cheng; Wu, Yan-Dong; Wang, Li-Sheng] Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Peoples R China.;[Tang, Bo-Cheng] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, State Key Lab Chem Biol & Drug Discovery, Kowloon, Hong Kong 999077, Peoples R China.
通讯机构:
[Wu, AX ] C;Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Natl Key Lab Green Pesticide, Wuhan 430079, Peoples R China.
摘要:
Abstract A I2‐DMSO mediated approach to introduce −OCD3 into pyrroles in situ via multicomponent cascade cyclization reaction using methyl ketones, aniline, ethyl benzoylacetate and CD3OD as readily available substrates is reported. This process realizes introduction of −OCD3 into the Hantzsch pyrrole synthesis and synthesis of deuterated alkoxy‐substituted pyrroles with formation of one C−C bond, one C−O bond and two C−N bonds in one pot. Notably, this conversion has good substrate compatibility (62 examples) and eliminates of the need for anhydrous and anaerobic operation.
通讯机构:
[Wu, AX ] C;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
摘要:
2-Hydroxy-4-morpholin-2,5-diarylfuran-3(2H)-one derivatives were constructed sequentially using iodine and zinc dust from simple and readily available methyl ketone and morpholine as the starting materials. Under mild conditions, C-C, C-N, and C-O bonds formed in a one-pot synthesis. A quaternary carbon center was successfully constructed, and the active drug fragment morpholine was introduced into the molecule.
期刊:
JOURNAL OF ORGANIC CHEMISTRY,2023年88(15):11150-11160 ISSN:0022-3263
通讯作者:
Wu, AX;Gao, M
作者机构:
[Lei, Shuang-Gui; Wu, An-Xin; Zhou, You; Chen, Ting; Yu, Zhi-Cheng; Wu, Yan-Dong; Wang, Li-Sheng] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Hubei, Peoples R China.;[Gao, Meng] South China Univ Technol, Natl Engn Res Ctr Tissue Restorat & Reconstruct, Sch Mat Sci & Engn, Key Lab Biomed Mat & Engn,Minist Educ, Guangzhou 510006, Peoples R China.
通讯机构:
[Wu, AX ] C;[Gao, M ] S;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Hubei, Peoples R China.;South China Univ Technol, Natl Engn Res Ctr Tissue Restorat & Reconstruct, Sch Mat Sci & Engn, Key Lab Biomed Mat & Engn,Minist Educ, Guangzhou 510006, Peoples R China.
摘要:
A novel multicomponent cascade cyclization reaction in one pot for the preparation of pyrido[3,2-a]phenoxazin-5-ones from simple o-aminophenols, paraformaldehyde, and enaminones has been established. It is noteworthy that o-aminophenol plays multiple roles serving as both a bis-nucleophile and an iminoquinone precursor, which can in situ generate aminophenoxazinones to undergo the Povarov reaction for the first time to yield pyrido[3,2-a]phenoxazin-5-ones with a high efficiency. Moreover, the photoluminescence of pyrido[3,2-a]phenoxazin-5-ones has polarity sensitivity and features aggregation-induced emission (AIE) characteristics, which is promising for bioimaging and theranostic applications.
通讯机构:
[Qun Cai; Yi Liu] C;[An-Xin Wu] K;Coal Conversion and New Carbon Materials Key Laboratory of Hubei Province, School of Chemistry and Chemical Engineering, Wuhan University of Science and Technology, Wuhan 430081, P. R. China<&wdkj&>School of Chemical and Environmental Engineering, Wuhan Polytechnic University, Wuhan 430023, P. R. China<&wdkj&>Coal Conversion and New Carbon Materials Key Laboratory of Hubei Province, School of Chemistry and Chemical Engineering, Wuhan University of Science and Technology, Wuhan 430081, P. R. China<&wdkj&>Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. China
摘要:
A transition-metal-free formal (4 + 2) cycloaddition for the direct assembly of acridone derivatives has been developed from simple and easily accessible o-aminobenzamides and 2-(trimethylsilyl)aryl triflates. The base played an important role in the selective controlled synthesis of N-H and N-aryl acridones. A preliminary study on the fluorescence properties of N-aryl acridones demonstrated that they could be used as fluorescent materials with a broad emission range.