4.6 Article

Palladium-catalyzed one pot 2-arylquinazoline formation via hydrogen-transfer strategy

期刊

ORGANIC & BIOMOLECULAR CHEMISTRY
卷 12, 期 39, 页码 7792-7799

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ob01296h

关键词

-

资金

  1. National Natural Science Foundation of China [21372187]
  2. New Century Excellent Talents in University from Ministry of Education of China [NCET-11-0974]
  3. Research Fund for the Doctoral Program of Higher Education of China [20124301110005]
  4. Scientific Research Foundation for Returned Scholars, Ministry of Education of China [2011-1568]

向作者/读者索取更多资源

The palladium catalytic system was first applied to 2-arylquinazoline synthesis via hydrogen transfer methodology. Various (E)-2-nitrobenzaldehyde O-methyl oximes reacted easily with alcohols or benzyl amines to provide N-heterocyclic compounds in good to high yields. Similarly, the heterocyclic products could be prepared by the reaction of 1-(2-nitrophenyl)ethanone, urea and benzyl alcohols. In these reactions, the nitro group was reduced in situ by hydrogen generated from the alcohol dehydrogenation step.

作者

我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.6
评分不足

次要评分

新颖性
-
重要性
-
科学严谨性
-
评价这篇论文

推荐

Article Chemistry, Multidisciplinary

Lewis acid-catalyzed 2-arylquinazoline formation from N '-arylbenzimidamides and paraformaldehyde

Xiufang Cheng, Huamin Wang, Fuhong Xiao, Guo-Jun Deng

GREEN CHEMISTRY (2016)

Article Chemistry, Organic

Functionalized Tetrahydropyridines by Enantioselective Phosphine-Catalyzed Aza-[4+2] Cycloaddition of N-Sulfonyl-1-aza-1,3-dienes with Vinyl Ketones

Huamin Wang, Wei Zhou, Mengna Tao, Anjing Hu, Junliang Zhang

ORGANIC LETTERS (2017)

Article Chemistry, Organic

Iron-Catalyzed One-Pot 2,3-Diarylquinazolinone Formation from 2-Nitrobenzamides and Alcohols

Huamin Wang, Xiangxiang Cao, Fuhong Xiao, Saiwen Liu, Guo-Jun Deng

ORGANIC LETTERS (2013)

Article Chemistry, Organic

Palladium-Catalyzed Phthalazinone Synthesis Using Paraformaldehyde as Carbon Source

Huamin Wang, Jinhui Cai, Huawen Huang, Guo-Jun Deng

ORGANIC LETTERS (2014)

Article Chemistry, Multidisciplinary

Phosphine-Catalyzed Difunctionalization of beta-Fluoroalkyl alpha,beta-Enones: A Direct Approach to beta-Amino alpha-Diazo Carbonyl Compounds

Huamin Wang, Li Zhang, Youshao Tu, Ruiqi Xiang, Yin-Long Guo, Junliang Zhang

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Phosphine-Catalyzed Enantioselective Dearomative [3+2]-Cycloaddition of 3-Nitroindoles and 2-Nitrobenzofurans

Huamin Wang, Junyou Zhang, Youshao Tu, Junliang Zhang

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Multidisciplinary Sciences

Catalytic Enantiodivergent Michael Addition by Subtle Adjustment of Achiral Amino Moiety of Dipeptide Phosphines

Huamin Wang, Xiuzheng Li, Youshao Tu, Junliang Zhang

ISCIENCE (2020)

Article Chemistry, Organic

Phosphine-Catalyzed Atroposelective Formal [3+2] Cycloaddition Desymmetrization of N-Arylmaleimides

Huamin Wang, Yibo Wei, Yuqiang Li, Shuangshuang Long, Li-Juan Sun, Shixiong Li, Ying-Wu Lin

Summary: A new strategy for the enantioselective synthesis of axially chiral N-aryl succinimides was developed using [3 + 2] annulation of MBH carbonates and N-aryl maleimides under chiral phosphine. This process allows for the efficient construction of stereogenic carbon centers and remote C-Ar-N atropisomeric chirality. The method exhibits mild reaction conditions, high efficiency, scalability, and a broad substrate scope.

ORGANIC LETTERS (2022)

Article Chemistry, Inorganic & Nuclear

Exploiting and Engineering Neuroglobin for Catalyzing Carbene N-H Insertions and the Formation of Quinoxalinones

Li-Juan Sun, Huamin Wang, Jia-Kun Xu, Shu-Qin Gao, Ge-Bo Wen, Ying-Wu Lin

Summary: This study presents the design and construction of a double mutant human neuroglobin (Ngb) that can efficiently catalyze carbene N-H insertions for aromatic amine and o-phenylenediamine derivatives, leading to high yields and total turnover numbers. It also demonstrates the first example of quinoxalinone formation catalyzed by an engineered heme enzyme.

INORGANIC CHEMISTRY (2023)

Article Chemistry, Organic

Synthesis of CF3-Containing 2-Imidazolines and Imidazoles via a Iodide-Promoted [3+2] Cyclization Reaction

Huamin Wang, Wenjing Niu, Yongjun He, Yibo Wei, Xianxian Li, Ying-Wu Lin

Summary: We report a general and effective system for the cyclization of beta-trifluoromethyl enones with amidines using 1,3-diiodo-5,5-dimethylhydantoin (DIH) as a catalyst. This reaction provides a range of trifluoromethylated 2-imidazolines in high yields and good diastereoselectivities, with good tolerance towards functional groups. Additionally, a one-pot synthesis of trifluoromethylated imidazoles via sequential cyclization and oxidation is demonstrated. The reaction mechanism is verified by ESI-MS studies, confirming a reasonable proposed mechanism.

JOURNAL OF ORGANIC CHEMISTRY (2023)

Article Chemistry, Multidisciplinary

Divergent functionalization of α,β-enones: catalyst-free access to β-azido ketones and β-amino α-diazo ketones

Youshao Tu, Honglin Dong, Huamin Wang, Yuhui Ao, Yu Liu

Summary: A method for azidation of beta-fluoroalkyl alpha,beta-unsaturated ketones has been developed, allowing access to a wide variety of fluorinated nitrogenous carbonyl compounds. The strategy does not involve any metallic or organic catalysts, and the choice of solvents can modulate the reaction outcomes to produce either beta-azido ketones or beta-amino alpha-diazo ketones. The reaction system is environmentally friendly, operates under mild conditions, is simple, and exhibits excellent functional group tolerance.

CHEMICAL COMMUNICATIONS (2021)

Article Chemistry, Multidisciplinary

Chiral bifunctional bisphosphine enabled enantioselective tandem Michael addition of tryptamine-derived oxindoles to ynones

Tiantian Cong, Huamin Wang, Xiuzheng Li, Hai-Hong Wu, Junliang Zhang

CHEMICAL COMMUNICATIONS (2019)

Article Chemistry, Multidisciplinary

Ferrocene Derived Bifunctional Phosphine-Catalyzed Asymmetric Oxa-[4+2] Cycloaddition of α-Substituted Allenones with Enones

Huamin Wang, Weike Lu, Junliang Zhang

CHEMISTRY-A EUROPEAN JOURNAL (2017)

Article Chemistry, Organic

Catalyst-free photo-induced aerobic radical synthesis of lactams from N-alkenyl trichloroacetamides in 2-methyltetrahydrofuran as the radical initiator under violet light

Faiza Diaba, Gisela Trenchs

Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.

ORGANIC & BIOMOLECULAR CHEMISTRY (2024)

Article Chemistry, Organic

Synthesis of mixed phosphorotrithioates via thiol coupling with bis(diisopropylamino)chlorophosphine and sulphenyl chloride

Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed

Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.

ORGANIC & BIOMOLECULAR CHEMISTRY (2024)

Article Chemistry, Organic

Catalyst-free assembly of a polyfunctionalized 1,2,4-triazole-fused N-heterocycle, 6-acylated pyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine

Hyunjin Oh, Ikyon Kim

Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.

ORGANIC & BIOMOLECULAR CHEMISTRY (2024)

Article Chemistry, Organic

Synthesis of sulfinamides via photocatalytic alkylation or arylation of sulfinylamine

Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li

Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.

ORGANIC & BIOMOLECULAR CHEMISTRY (2024)

Article Chemistry, Organic

Two distinct protocols for the synthesis of unsymmetrical 3,4-disubstituted maleimides based on transition-metal catalysts

Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst

Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.

ORGANIC & BIOMOLECULAR CHEMISTRY (2024)

Article Chemistry, Organic

Conversion of amino-terephthalonitriles to multi-substituted single benzene fluorophores with utility in bioimaging

Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar

Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.

ORGANIC & BIOMOLECULAR CHEMISTRY (2024)

Review Chemistry, Organic

Microbial alcohol dehydrogenases: recent developments and applications in asymmetric synthesis

Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan

Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.

ORGANIC & BIOMOLECULAR CHEMISTRY (2024)