通讯机构:
[Wu, YD; Wu, AX] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.
摘要:
A N–H/α,β-C(sp3)-trifunctionalization of l-proline, proceeding through an iodine-promoted consecutive decarboxylation/ring-opening/dicyclization process, is achieved. This strategy affords structurally diverse fused N-heterocycles in good yields with a wide substrate scope. Preliminary mechanistic studies indicate that catabolism of l-proline might be involved in this cascade reaction and the in situ generated intermediate 4-aminobutanal was identified as the key intermediate. Notably, this domino strategy enriches the reactivity of versatile l-proline in the synthesis of fused heterocycles.
作者机构:
[Feng, Ling-ling; Huang, Chun; Feng, AX; Wang, Can; Feng, An-Xin; Zhou, You; Geng, Xiao; Bao, Yang; Zhao, Peng] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.;[Feng, An-Xin] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China.
通讯机构:
[Feng, LL; Feng, AX] C;[Feng, An-Xin] L;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.;Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China.
摘要:
We report an I2/FeCl3-co-promoted formal [2 + 2+1] annulation of aryl methyl ketones, 2-aminobenzyl alcohols, and p-toluenesulfonylmethyl isocyanide (TosMIC) by neighboring group (-CH2OH) assistance. This is a novel example of using the Van Leusen reagent as a unique C1N1 "two-atom synthon" in the synthesis of imidazoles. Preliminary mechanism studies showed that TsCH2NH2 might be the key intermediate in this reaction. Furthermore, this reaction not only unlocks a novel strategy for imidazole synthesis, but also exploits a new reactivity of TosMIC.
摘要:
We herein describe an efficient copper-catalyzed three-component domino protocol used to prepare 2,1-benzoisoxazole-containing 1,2,3-triazoles from commercially available o-bromoacetophenones, aldehydes, and sodium azide. This domino process involves Aldol condensation, copper-catalyzed azide-chalcone oxidative cyclization, 1,2,3-triazole-assisted azidation, and denitrogenative cyclization sequences. The formed compounds could be considered as benzo[c]isoxazole-functionalized combretastatin A-4 triazole analogues, which might be potential applications in the discovery of a new anticarcinogen.
通讯机构:
[Shu, Wen-Ming] Y;[Wu, An-Xin] C;Yangtze Univ, Coll Chem & Environm Engn, Jingzhou 434023, Peoples R China.;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China.
摘要:
A trifluoroacetic acid (TFA)-mediated cascade oxidation/1,3-dipolar cycloaddition reaction of stabilized pyridinium salts with dimethyl sulfoxide (DMSO) has been developed in the presence of K2S2O8 and trimethylethylenediamine (TMEDA). In this transition-metal-free reaction, DMSO acts as a one-carbon source, thus providing a convenient method for the efficient and direct synthesis of various indolizine derivatives.
摘要:
An efficient and practical isatin-based oxidative domino protocol has been developed for the facile synthesis of 2-aminobenzamides and 2-aminobenzoates. The robust nature of this reaction system is reflected by accessible starting materials, room temperature and high-yield gram-scale synthesis. (C) 2019 Elsevier Ltd. All rights reserved.
期刊:
JOURNAL OF ORGANIC CHEMISTRY,2019年84(12):8322-8329 ISSN:0022-3263
通讯作者:
Wu, An-Xin
作者机构:
[Zhao, Peng; Wu, Xia; Geng, Xiao; Wang, Can; Zhou, You; Wu, Yan-Dong; Wu, An-Xin] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China
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:
An I-2/PhI(OAc)(2) copromoted strategy using dimethyl sulfoxide as an "S/C2/O" source for preparing alpha-dicarbonylsulfoximine derivatives is reported. This process involves oxidative coupling to construct a C-N bond and electrophilic amination of dimethyl sulfoxide to afford an N = S bond, with dimethyl sulfoxide present in the final product as an intact molecule. Furthermore, tetramethylene sulfoxide as a solvent is also compatible with this amination reaction.
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 rongalite-mediated three-component radical annulation reaction to furnish fully substituted pyrazoles from aryldiazonium salts and alpha,beta-unsaturated aldehydes or ketones under metal- and oxidant-free conditions at room temperature has been developed. In this transformation, aryldiazonium salts served as the precursor of both the aryl and aryl hydrazine units. Mechanistic investigations indicated that rongalite could act as a radical initiator and reducing reagent simultaneously in the reaction.
作者机构:
[Wang, Miao; Wang, Zi-Xuan; Xiang, Jia-Chen; Ma, Jin-Tian; Wu, An-Xin; Wu, Yan-Dong] 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, Gansu, Peoples R China.
通讯机构:
[Wu, An-Xin] C;[Wu, An-Xin] L;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Hubei, Peoples R China.;Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China.
摘要:
The one-pot total synthesis of evodiamine and its analogues is achieved using a three-component reaction. Through continuous biscyclization, various readily available substrates with good functional group tolerance were easily incorporated into biologically active quinazolinocarboline backbones. The use of triethoxymethane as a cosolvent was crucial for this quick and straightforward transformation.
通讯机构:
[Wu, An-Xin] C;[Jia, Feng-Cheng] W;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Hubei, Peoples R China.;Wuhan Inst Technol, Sch Chem & Environm Engn, Wuhan 430205, Hubei, Peoples R China.
摘要:
A practical copper-catalyzed multicomponent reaction has been developed for the synthesis of 1H-[1,2,3]triazolo[4,5-c]quinoline derivatives from commercially available 2-bromobenzaldehydes, aryl methyl ketones, and sodium azide. This protocol integrated consecutive base-promoted condensation, [3 + 2] cycloaddition, copper-catalyzed SNAr, and denitrogenation cyclization sequences. Preliminary mechanistic studies revealed that CuBr2 acted as a multifunctional catalyst to streamline this domino process. The mild catalytic system enabled effective construction of one C–C and four C–N bonds in one operation.
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:
The increasing importance of enzyme mimics in organic synthesis inspired us to design a novel biomimetic synthesis of beta-carboline alkaloids directly from tryptophan and a second amino acid. This novel one-pot protocol utilizes abundant and readily available starting materials and thus presents a green and user-friendly alternative to conventional methods that rely on stepwise synthesis. Driven by molecular iodine and TFA, decarboxylation, deamination, Pictet-Spengler reaction, and oxidation reactions proceeded sequentially, transforming biomass amino acids into value-added alkaloid motifs.
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:
An efficient base-promoted C(sp3)–H bond functionalization strategy for the synthesis of multisubstituted chromans from the formal [3+3] cycloaddition of benzo[c]oxepines and electron-rich phenols has been developed. The corresponding 4H-chromenes can be easily obtained in excellent yields by simple filtration from chromans. Preliminary mechanistic studies indicate that the C–O bond cleavage is the key step for the C(sp3)–H bond functionalization and that this reaction could have occurred through tandem C–O bond cleavage/Michael addition/annulation reactions.
通讯机构:
[Wu, Anxin] C;[Yang, Chuluo] W;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China.;Wuhan Univ, Dept Chem, Wuhan 430072, Hubei, Peoples R China.;Wuhan Univ, Hubei Key Lab Organ & Polymer Optoelect Mat, Wuhan 430072, Hubei, Peoples R China.
摘要:
A molecular iodine-mediated formal [2+1+1+1] cycloaddition for the efficient synthesis of pyrrolo[2,1-a]isoquinolines from acetophenones, 1,2,3,4-tetrahydroisoquinoline (THIQ) and DMSO has been developed. Mechanistic studies revealed that DMSO served as the methylene source, and this novel protocol involves intermolecular cycloaddition of two in situ generated intermediates that enable efficient formation of one C-N bond and three C-C bonds via multiple sequential C-H functionalizations.
摘要:
A simple and convenient method for N-aminosulfonamide synthesis from the cross-coupling of aryldiazonium tetrafluoroborates and rongalite under metal-free, oxidant-free, and room-temperature conditions is reported. This method does not require an external amine source, with the aryldiazonium tetrafluoroborates participating as both an aryl radical and a potential amine source in the transformation. Mechanistic studies revealed that rongalite could act as a radical initiator, a sulfur dioxide surrogate and a reducing reagent simultaneously in this reaction.
通讯机构:
[Shu, Wen-Ming] Y;[Wu, An-Xin] C;Yangtze Univ, Coll Chem & Environm Engn, Jingzhou 434023, Peoples R China.;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Hubei, Peoples R China.
摘要:
An interesting σ-bond insertion/benzannulation reaction for the synthesis of polysubstituted naphthalene derivatives has been developed from readily accessible ketones, arynes, and alkynoates. This practical and transition-metal-free method provides a novel route to diverse naphthalenes through a substrate-controlled rearrangement reaction with the cleavage of C–C bonds.
通讯机构:
[Wu, An-xin] C;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
摘要:
A novel iodine-promoted oxidative cross-coupling/cyclization of 2-(pyridin-2-yl)acetate derivatives and methyl ketones via the cleavage of multiple Csp3–H bonds has been developed, which also achieved efficient cleavage of a C–C bond in the 2-(pyridin-2-yl)acetate derivatives. This protocol represents an elegant molecular fragment assembly of diverse 3-(pyridin-2-yl)indolizines via a formal [3 + 1 + 1] annulation. Notably, the pyridine derivatives serve two pivotal roles to provide two fragments to construct 3-(pyridin-2-yl)indolizine skeletons, rather than the single role in building common indolizines.
作者机构:
[蔡群; 李登奎; 吴安心] Key Laboratory of Pesticide & Chemical Biology,Ministry of Education,College of Chemistry,Central China Normal University
会议名称:
中国化学会全国第十二届有机合成化学学术研讨会
会议时间:
2015-10-15
会议地点:
中国广西桂林
会议论文集名称:
中国化学会全国第十二届有机合成化学学术研讨会论文摘要集
摘要:
Naphthalene derivatives are an important class of compounds that can be found in numerous natural products and broadly used in medicinal chemistry,particularly as antiviral,anticancer,antibacterial,an
作者机构:
[Wang Miao; Wu An-Xin] Key Laboratory of Pesticide & Chemical Biology,Ministry of Education,College of Chemistry,Central China Normal University
会议名称:
中国化学会第十三届全国有机合成化学学术研讨会
会议时间:
2016-10-13
会议地点:
中国江苏扬州
摘要:
Rongalite(Na+HOCH2 SO2-· 2H2O) is a useful and cheap industrial product which has been widely used in the dye,rubber,and veterinary industries.It is also used as a versatile reagent in synthetic c