作者机构:
[Wu, An-Xin; Ma, Jun-Rui; Wu, Yan-Dong; Zheng, Kai-Lu; Shu, Wen-Ming] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;[Wu, An-Xin] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China.
通讯机构:
[Wu, An-Xin] L;[Wu, YD; Wu, AX] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China.
摘要:
A one-pot acid-mediated reaction has been developed for the N–H/α,β-C(sp3)–H trifunctionalization of pyrrolidine without any metallic reagents or external oxidants. This reaction involves the intermolecular [3 + 2] cycloaddition of in situ-generated azomethine ylides with acrylic esters to provide facile access to 2,3-dihydro-1H-pyrrolizine derivatives in high yields under mild conditions.
作者机构:
[Wu, An-Xin; Jia, Feng-Cheng; Zhou, Zhi-Wen; Xu, Cheng; Cai, Qun; Li, Deng-Kui] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Hubei, Peoples R China.;[Wu, An-Xin] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China.
通讯机构:
[Wu, An-Xin] C;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Hubei, Peoples R China.
摘要:
A highly efficient multicomponent domino protocol has been developed for the synthesis of 5-phenyl-[1,2,3]triazolo[1,5-c]quinazolines from simple and readily available (E)-1-bromo-2-(2-nitrovinyl)benzenes, aldehydes, and sodium azide. This elegant domino process involved consecutive [3 + 2] cycloaddition, copper-catalyzed SNAr, reduction, cyclization, and oxidation sequences. Notably, sodium azide acted as a dual nitrogen source in the construction of this novel fused N-heterocycle.
通讯机构:
[Yin, Jun] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
摘要:
Tetraphenylethene (TPE) with aggregation-induced emission (AIE) behavior as a popular backbone is applied widely in the construction of functional supramolecular systems. In this work, a TPE-based linear molecule having amide and amine units is synthesized. Its ammonium template is used to construct the N-hetero crown ether-based [2] rotaxane by the template-directed clipping approach. Their structures are well-characterized by NMR, MALDI-TOF-MS and elemental analysis. Owing to the existence of the amide unit, [2] rotaxane possesses the function of a molecular shuttle. The shuttling motion of the macrocycle component between the ammonium station and the amide station can be driven by external acid-base stimuli in solution, accompanied by changes in visual behavior. Investigation on their AIE behavior shows that (1) ammonium reaches the aggregation state almost in the presence of same water with the deprotonated form of ammonium; (2) the [2] rotaxane that the macrocycle component locates at the site of ammonium forms the aggregation state in the presence of less water than the deprotonated [2] rotaxane that the macrocycle component locates at the site of the amide, attributed to stronger interaction between the crown ether component and the TPE unit of the template component when the distance between the two is shorter. The result indicates that the shuttling motion of the macrocycle component can adjust the aggregation state of AIE molecules.
作者机构:
[Wu, An-Xin; Cheng, Yan; Wang, Miao; Xiang, Jia-Chen] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Wu, An-Xin] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.
摘要:
A new process has been developed for the selective construction of 2,6-disubstituted, 2,4,6-trisubstituted, and 3,5-disubstituted pyridines based on the catabolism and reconstruction behaviors of amino acids. Molecular iodine was used as a tandem catalyst to trigger the decarboxylation–deamination of amino acids and to promote the subsequent formation of the pyridine products.
作者机构:
[Wu, An-Xin; Sun, Hui-Ying; Ma, Jun-Rui; Wang, Mei; Zheng, Kai-Lu; Shu, Wen-Ming] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Hubei, Peoples R China.;[Wu, An-Xin] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China.
通讯机构:
[Wu, An-Xin] C;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Hubei, Peoples R China.
摘要:
A multicomponent reaction has been developed for the synthesis of polyfunctional pyrazole derivatives from readily available arylglyoxal monohydrates, tosylhydrazine, and aldehydes or ketones. This synthetic method has significant advantages in broad substrate scope, excellent regioselectivity, and simple operation.
作者机构:
[Wu, An-Xin; Jia, Feng-Cheng; Zhou, Zhi-Wen; Xu, Cheng; Cai, Qun; Li, Deng-Kui] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.;[Wu, An-Xin] Lanzhou Univ, Dept Chem, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China.
通讯机构:
[Wu, An-Xin] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
摘要:
A copper-catalyzed domino protocol for the synthesis of 2-(1,3,4-oxadiazol-2-yl)aniline derivatives has been developed from simple and available isatins and hydrazides. This domino process integrated consecutive condensation, base-promoted ring-opening and the key copper-catalyzed decarboxylative coupling for intramolecular C-O bond formation.
作者机构:
[Wu, Anxin; Zhang, Jingjing; Liu, Shan; Gao, Qinghe; Wu, Xia] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
通讯机构:
[Wu, Anxin] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
摘要:
A new strategy for the synthesis of 1,3,4-oxadiazoles was established through direct annulation of hydrazides with methyl ketones. It was found that the use of K2CO3 as a base achieves an unexpected and highly efficient C–C bond cleavage. This reaction is proposed to go through oxidative cleavage of Csp3–H bonds, followed by cyclization and deacylation.
摘要:
A novel method for the generation of o-quinodimethane (o-QDM) intermediates is reported using a mild and efficient base-promoted ring-opening of benzo[c]oxepines. Among the benzo[c]oxepines studied, indanone containing analogues demonstrated the greatest variety of reactivity. A number of decay modes were observed, in addition with trapping of the o-QDM intermediates using dienophiles for the synthesis of polysubstituted tetrahydronaphthalenes with high regioselectivity. This research provided a novel method to generate o-QDM intermediates from benzo[c]oxepine precursors.
摘要:
A highly efficient chemoselective synthesis of multifunctionalized tetrahydro-1H-pyrrolor[1,2-c]imidazole and tetrahydropyrrolo[1,2-c]thiazole derivatives has been established from arylglyoxal monohydrates, nitriles, and thioureas. A series of control experiments suggested that this reaction proceeded through the convergent integration of two self-sorting domino sequences. This synthetic strategy is promising for diversity-oriented synthesis of alkaloid analogues. (C) 2015 Elsevier Ltd. All rights reserved.
作者机构:
[Wu, Anxin; Zhang, Jingjing; Liu, Shan; Gao, Qinghe; Wu, Xia] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;[Xi, Hailing] State Key Lab NBC Protect Civilian, Beijing 102205, Peoples R China.;[Gao, Qinghe] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Gao, Qinghe] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
摘要:
An NH2CN-promoted convergent integration of three self-sorting domino sequences is described for the construction of 6-iodo-3-methylthioimidazo[1,2-a] pyridines from aryl methyl ketones and 2-aminopyridines. This strategy allows the construction of an imidazo[1,2-a] pyridine ring along with methylthiolation at C-3 and iodination at C-6. Preliminary mechanistic studies indicate that this process terminates at the iodination stage without Kornblum oxidation in the presence of I-2 and DMSO.
作者机构:
[Wu, An-Xin; Ma, Jun-Rui; Ni, Fan; Zheng, Kai-Lu; Shu, Wen-Ming] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;[Yin, Guo-Dong] Hubei Normal Univ, Hubei Collaborat Innovat Ctr Rare Met Chem, Hubei Key Lab Pollutant Anal & Reuse Technol, Huangshi 435002, Peoples R China.
通讯机构:
[Yin, Guo-Dong] H;Hubei Normal Univ, Hubei Collaborat Innovat Ctr Rare Met Chem, Hubei Key Lab Pollutant Anal & Reuse Technol, Huangshi 435002, Peoples R China.
摘要:
A highly efficient method for the synthesis of 2-hydroxy-2,3-dihydrofuran derivatives from 1,4-enediones and phenacyl pyridinium halides via a domino reaction has been developed. This is a simple and beneficial strategy for the construction of 2-hydroxy-2,3-dihydrofuran compounds from readily available starting materials under mild conditions. Moreover, the application of this reaction provides a straightforward and practical route for the synthesis of the novel 4-(1H-pyrazol-4-yl)pyridazine skeleton.
作者机构:
[Wu, Anxin; Zhang, Jingjing; Liu, Shan; Gao, Qinghe; Wu, Xia] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
通讯机构:
[Wu, Anxin] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
摘要:
A highly efficient I2-catalyzed Povarov-type reaction of methyl ketones, arylamines, and α-ketoesters is developed. This reaction utilizes a catalytic amount of HI coproduct as a promoter for the synthesis of substituted quinolones. This simple procedure represents an interesting new form of reactivity for the Povarov reaction with good functional group compatibility.
作者机构:
[Wu, An-Xin; Ma, Jun-Rui; Zheng, Kai-Lu; Shu, Wen-Ming] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
通讯机构:
[Wu, An-Xin] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
摘要:
A transition-metal-free multicomponent benzannulation reaction was developed from readily available ketones, nitro-olefins, and diester acetylenedicarboxylate. This approach provides a straightforward and efficient way to construct polysubstituted benzene derivatives under mild conditions in high yields.
通讯机构:
[Wu, An-Xin] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China.
摘要:
A highly efficient Fe/Cu relay-catalyzed domino protocol has been developed for the synthesis of 2-phenylquinazolin-4-amines from commercially available ortho-halogenated benzonitriles, aldehydes, and sodium azide. This elegant domino process involved consecutive iron-mediated [3 + 2] cycloaddition, copper-catalyzed SNAr, reduction, cyclization, oxidation, and copper-catalyzed denitrogenation sequences. The formed structure is the privileged core in drugs and bioactive molecules.
摘要:
An efficient iodine-mediated multipathway coupled domino reaction has been developed for the synthesis of thiobenzamides from benzylamines, benzylamines/aldehydes, and N-alkyl benzylamines under the same reaction conditions. This approach combines two consecutive domino processes in one pot using iodine as the oxidant. (C) 2015 Elsevier Ltd. All rights reserved.
摘要:
A molecular iodine mediated oxidative cross-coupling of beta-keto ester sp(3) C-H with 1H-indole sp(2) C-H was developed for the synthesis of indolo[2,3-b]carbazoles. A self-sequenced iodination/Kornblum oxidation/hydrolyzation/decarboxylative/deacylation/aromatization mechanism has been proposed as a possible reaction sequence to account for the results observed in this study. (C) 2015 Elsevier Ltd. All rights reserved.