作者机构:
[Wu, Anxin; Zhang, Jingjing; Liu, Shan; Gao, Qinghe; Ding, Kerong; Wu, Xia] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;[Wu, Anxin] 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:
[Wu, Anxin] 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:
A highly efficient molecular iodine catalyzed oxidative amidation of aryl methyl ketones with formamidine hydrochloride has been developed. This reaction represents a novel strategy for the synthesis of free (N-H) alpha-ketoamides. Based on the experimental results, a self-sequenced iodination/Kornblum oxidation/amidation/oxidation/decarbonylation mechanism was proposed.
作者机构:
[Wu, Anxin; Wang, Miao; Meng, Xianggao; Xiang, Jiachen; Wang, Jungang] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China.;[Wu, Anxin] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
通讯机构:
[Wu, Anxin] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
摘要:
This paper described a decarboxylative deaminative dual-coupling reaction of amino acids with indoles to afford BIM scaffolds and its further application to the one-pot total synthesis of natural products. This method featured a stimulating example of activating amino acids in one pot as multi-carbon building blocks for transformation into final targets which are equipped with amino acid side chain backbones.
作者机构:
[Wu, Anxin; Wang, Miao; Meng, Xianggao; Xiang, Jiachen; Wang, Jungang] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
通讯机构:
[Wu, Anxin] C;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
关键词:
One-pot total synthesis;Amino acid;Iodination;Kornblum oxidation;5-(3-Indolyl)oxazole alkaloid
摘要:
In this work, we accomplished the first total synthesis of chiral alkaloid pimprinol A and the facile construction of its natural congeners: pimprinine, pimprinethine, pimprinaphine, WS-30581A, WS-30581B, laboradorin 1, uguenenazole, balsoxine, texamine in one-pot from commercially available starting materials including amino acids. Further investigating into the mechanism revealed that this improved transformation was achieved by the integration of iodination, Kornblum oxidation, condensation, decarboxylation, annulation, and oxidation reaction sequence. (C) 2014 Elsevier Ltd. All rights reserved.
摘要:
Water-controlled and phosphine-mediated selective synthesis of saturated 1,4-diketones and tetrasubstituted furans has been developed directly from 1,4-enediones. Saturated 1,4-diketones were selectively obtained in acetone with water as an additive, whereas tetrasubstituted furans were selectively obtained in anhydrous 1,2-dichloroethane. A large variety of functional groups are tolerated under these reaction conditions, including electron-rich, electron-poor, halogen, and heteroaryl substituents. This method also has significant advantages in easily available substrates, mild reaction conditions, and high reaction efficiency. (C) 2014 Elsevier Ltd. All rights reserved.
作者机构:
[Wu, Anxin; 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 and selective molecular iodine-promoted oxidative cross-coupling/annulation between 2-naphthols and methyl ketones has been realized. The reaction successfully constructed a new quaternary carbon center within 3(2H)-furanones. Our synthetic strategy provided an in situ iodination-based oxidative coupling pathway. Based on the experimental results, a self-sequenced iodination/Kornblum oxidation/Friedel-Crafts/oxidation/cyclization mechanism was proposed.
摘要:
An efficient and practical method for the synthesis of cyano, sulfonyl and phosphoryl substituted naphthalene derivatives via the rearrangement aromatization of benzo[c]oxepine has been developed. The system holds the advantages of metal catalysts free, and mild reaction conditions. (C) 2014 Elsevier Ltd. All rights reserved.
作者机构:
[Wu, An-Xin; Jia, Feng-Cheng; Xu, Cheng; Cai, Qun] Cent China Normal Univ, Minist Educ, Coll Chem, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
通讯机构:
[Wu, An-Xin] C;Cent China Normal Univ, Minist Educ, Coll Chem, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
摘要:
A highly efficient three-component domino protocol has been developed for the synthesis of [1,2,4]triazolo[1,5-b]isoquinolin-5(1H)-ones from simple and readily available o-halogenated benzohydrazides, aldehydes and nitriles. This domino process involves sequential selective condensation, copper-catalyzed intermolecular C-arylation and bicyclization. Notably, the use of ligands and anaerobic conditions can be avoided in this reaction.
作者机构:
[Wu, Anxin; Liu, Shan; Gao, Qinghe; Wu, Xia] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
通讯机构:
[Wu, Anxin] C;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
摘要:
A highly efficient molecular iodine mediated formal [3 + 2 + 1] cycloaddition reaction for the direct synthesis of substituted quinolines from methyl ketones, arylamines, and styrenes is developed. The methyl group of the methyl ketone represents uniquely reactive input in the Povarov reaction. A self-sequenced iodination/Kornblum oxidation/Povarov/aromatization mechanism has been proposed as a possible reaction sequence to account for the results observed in this study.
作者机构:
[Wu, An-Xin; Yang, Yan; Ni, Fan; Ma, Jun-Rui; 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] 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:
[Wu, An-Xin] 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:
A Bronsted acid promoted C-C bond cleavage method for the synthesis of novel 2-amino-5-aroylmethylthiazole derivatives has been directly developed from 1,4-enediones and thioureas through selfsequenced thio-Michael-addition, intramolecular selective cyclization, dehydration/aromatization, and C-C bond cleavage reactions. It is noteworthy that this reaction has significant advantages in simple reagents, under environmentally benign conditions and with excellent yields. This highly efficient method is also a highly attractive alternative for the preparation of PLTP, CETP inhibitors and novel biheterocycles.
作者机构:
[Wu, Anxin; Liu, Shan; Gao, Qinghe; Wu, Xia] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
通讯机构:
[Wu, Anxin] C;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
摘要:
An iodine-catalyzed oxidative cross-coupling of C-H/N-H has been demonstrated. This simple and efficient approach constructed alpha-ketoimides in good to excellent yields from methyl ketones and benzamidines hydrochloride under metal-free and peroxide-free conditions. This synthetic strategy was achieved via an in situ iodination-based oxidative coupling pathway.
摘要:
An I-2-promoted three-component coupling reaction was described for the construction of 3-(methylthio) -4-aryl-1H-pyrrole-2,5-diones from methyl ketones with acetonitrile and DMSO. This transformation involved the in situ generation and application of alpha-ketoimides. Furthermore, DMSO was converted to DMS in situ, which subsequently served as a methylthiolation reagent in the reaction. To the best of our knowledge, this protocol provided the first known example of convergent integration of three self-sorting domino sequences. (C) 2014 Elsevier Ltd. All rights reserved.
摘要:
An electronic tuning Nazarov-type cyclization protocol was proposed for the synthesis of polysubstituted-1-indanones from the readily available starting materials 1,4-enediones. AlCl3 was highlighted as the most efficient promoter for this reaction.
摘要:
An iodine-promoted selective synthesis has been developed for the construction of substituted aminothiazole from easily available aryl methyl ketones and thiourea under metal free conditions. This domino process involves the cleavage of C-H, C-O, C-S bonds and the formation of C-N, C-O, C-S bonds. (C) 2014 Elsevier Ltd. All rights reserved.
摘要:
A novel method for constructing trisubstituted imidazoles has been created using simple and readily available aromatic ketones, benzoins, and ammonium acetate as starting materials. The new synthetic strategy utilized a convergent integration of two self-labor domino sequences, providing a typical example for logical self-organization synthesis. (C) 2013 Elsevier Ltd. All rights reserved.
作者机构:
[Wu, Anxin; Lian, Mi; 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:
An I-2-promoted activation of carbon-carbon double bonds has been demonstrated. This simple and efficient domino process was utilized for the direct construction of alpha-hydroxyacetophenones in moderate to good yields from easily available styrenes at room temperature. This approach involved molecular iodine activation of carbon-carbon double bonds to form an iodonium intermediate. Moreover, TBHP was used as the sole effective oxidant and water was used as nucleophilic reagent in this reaction.
摘要:
A new process has been developed for the iodine-promoted sequential C(sp(3))-H bond functionalization of methyl ketones and acetamides. This reaction represents a novel annulation strategy for the synthesis of 3-(methylthio)-4-aryl-1H-pyrrole-2,5-diones, and involves an alpha-ketoimide as the key intermediate. Furthermore, DMSO was converted to DMS in situ, which served as the methylthiolation reagent in the reaction. This protocol constitutes an efficient and convenient method for the methylthiolation of substrates bearing a wide range of functional groups.