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Chiral iminophosphorane catalyzed asymmetric Henry reaction of α,β-alkynyl ketoesters

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Chinese Chemical Letters 2019年第8期30卷 1519-1522页

作者： Yanxia Zhang Xin-Yan Wu Jianwei Han Key Laboratory for Advanced Materials Institute of Fine ChemicalsSchool of Chemistry&Molecular EngineeringEast China University of Science and TechnologyShanghai 200237China Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis Shanghai Institute of Organic ChemistryThe Chinese Academy of SciencesShanghai 200032China

α,β-Alkynyl ketoesters were introduced to the enantioselective Henry reaction(nitroaldol condensation)with nitromethane catalyzed by tartaric acid derived chiral *** such,a variety of optically activeβ-nitro-substituted tertiary alcohols bearing alkyne moieties were obtained in good to excellent yields(42%–99%)and moderate to good level of enantiomeric excess(up to 87%ee).

关键词： Organocatalysis iminophosphorane Nitroaldol Henry reaction Alkynyl ketoesters

Synthesis and Crystal Structure of 2-(4’-Methylphenoxy)-5,8,9-trimethyl-3-phenyl Thieno[3′,2′:5,6]pyrido[4,3-d]pyrimidin-4-(3H)-one Hydrochloride

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Chinese Journal of Structural Chemistry 2006年第5期25卷 577-581页

作者： LIU Jian-Chao HE Hong-Wu DING Ming-Wu College of Chemistry Central China Normal University Wuhan 430079 China

The title compound 2-（4＇-methylphenoxy）-5,8,9-trimethyl-3-phenyl thieno[3＇,2＇：5,6] pyrido[4,3-d]pyrimidin-4（3H）-one hydrochloride （C26H23Cl4N3O2S, Mr = 583.33） has been determined by single-crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/c with a = 14.8442（ 11 ）, b = 11.5131 （8）, c = 17.2010（13） A, β = 113.7250（10）°, V = 2691.3（3） ,A^3, Z = 4, Dc = 1.440 g/cm^3, S = 1.094,μ = 0.547 mm^-1, F（000） = 1200, the final R = 0.0571 and wR = 0.1458. X-ray analysis reveals that the title compound combines with a molecule of dichloromethane by an intramolecular hydrogen bond. The thienopyridine ring is almost coplanar, and the dihedral angle between the thiophene plane and the pyridine plane is 0.6°.

关键词： thieno[3',2':5,6]pyrido[4,3-d]pyrimidin-4(3H)-one,triphenylphosphine iminophosphorane crystal structure

An efficient route for synthesis of 2-alkylamino benzo[b]thieno[3,2-d]pyrimidin-4(3H)-one

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Chinese Chemical Letters 2011年第4期22卷 443-446页

作者： Min Hui Cao Sheng Zhen Xu Chang Shui Chen College of Basic Science Huazhong Agricultural UniversityWuhan 430070China

The carbodiimide 2,obtained from the aza-Wittig reactions of iminophosphorane 1 with alkyl isocyanates,reacted with primary amino to give 2-alkylamino benzo[b]thieno[3,2-d]pyrimidin-4（3H）-ones 4 and *** formation me... 详细信息

关键词： Carbodiimides Aza-Wittig reaction iminophosphorane Isocyanates Synthesis

Facile Synthesis of Phosphorus N-Fluoroalkanesulfonyl Amidines by Cu-catalyzed One-pot Three-component Reaction

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Chinese Journal of Chemistry 2011年第12期29卷 2675-2680页

作者：张振华熊婉婷顾继伟朱士正 Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 345 Lingling Road Shanghai 200032 China

In the presence of Cu（I） and triethyl amine, one-pot three-component reaction of fluoroalkanesulfonyl azides, alkynes and iminophosphoranes in CH2Cl2 at room temperature gave a novel class of fluorinated phosphorus ... 详细信息

关键词： fluoroalkanesulfonyl azide iminophosphorane alkyne three-component reaction amidine

New Facile Synthesis of 2-Aryloxy-5-(2-furfurylidene)- 4H-imidazolin-4-ones

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Chinese Chemical Letters 2002年第10期13卷 942-944页

作者： Ming Wu DING Jing ZHU Su Fang SHI Xiao Peng LIU Institute of Organic Synthesis Central China Normal UniversityWuhan 430079 Department of Chemistry Central China Normal UniversityWuhan 430079 Center of Analysis and Testing Central China Normal UniversityWuhan 430079

Novel 2-aryloxy-5-(2-furfurylidene)-4H-imidazolin-4-ones 6 were synthesized by aza-Wittig reaction of vinyliminophosphorane 4 with phenyl isocyanate and subsequent condensation with Various substituted phenols in the presence of catalytic amount of potassium carbonate. The products are confirmed by H-1 NMR, MS, IR and elementary analysis.

关键词： H-Imidazolin-4-one aza-Wittig reaction iminophosphorane synthesis.

Efficient synthesis of 4(3H)-quinazolinones using a soluble polymeric support

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Chinese Chemical Letters 2008年第5期19卷 505-508页

作者： Chang Xie Hong Xia Li Ming Guo Liu Ming Wu Ding Key Laboratory of Pesticide ＆ Chemical Biology of Ministry of Education Central China Normal University Wuhan 430079 China

4（3H）-Quinazolinones have been synthesized from poly（ethylene glycol）（PEG） supported aza-Wittig reaction. 2-Dialkylamino- 4（3H）-quinazolinones 6 were synthesized efficiently by reaction of secondary amine with PEG-supported carbodiimides 4, which were obtained from aza-Wittig reaction of PEG-supported iminophosphoranes 3 with isocyanates.

关键词： 4(3H)-Quinazolinone Poly(ethylene glycol) supported Aza-Wittig reaction Carbodiimide iminophosphorane

Efficient Regioselective Synthesis of 3-1odoindole N-Carboximidamides and N-Carboximidoates by a Sequential Aza-Wittig/Iodine Induced Cyclization

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Chinese Journal of Chemistry 2012年第8期30卷 1807-1812页

作者：聂熠博段专丁明武 Key Laboratory of Pesticide&Chemical Biology of Ministry of Education Central China Normal UniversityWuhanHubei 430079China

3-Iodoindole N-carboximidamides and N-carboximidoates 4 were prepared regioselectively via a sequential aza-Wittig/iodine induced cyclization, starting from easily accessible 2-alkynylphenyl iminophosphorane, isocyana... 详细信息

关键词： indole aza-Wittig reaction iodine cyclization iminophosphorane

A Rapid Parallel Synthesis of 2-Dialkylamino-4(3H)-quinazolines

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Chinese Chemical Letters 2004年第3期15卷 280-283页

作者： MingWuDING YingLIU GuiFengZHANG ShangJunYANG CollegeofChemistry CentralChinaNormalUniversityWuhan430079

Dialkylamino-4(3H)-quinazolinones 4 were rapidly synthesized by a solution-phase parallel synthetic method, which includes aza-Wittig reaction of iminophosphorane 1 with aromatic isocynate to give carbodiimide 2 and s... 详细信息

关键词： H)-Quinazolinone aza-Wittig reaction iminophosphorane parallel synthesis.

Novel Tandem Three Consecutive Reactions: Aza-Wittig, Imine Condensation and Electrophilic Aromatic Substitution Strategy to Indolizine Synthesis

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International Journal of Organic Chemistry 2021年第2期11卷 55-71页

作者： Julio C. González-Rodríguez Carlos González-Romero Erick Cuevas-Yáñez Juan J. Mejía Vega Christopher K. Jankowski David Corona-Becerril Centro Conjunto de Investigación en Química Sustentable (CCIQS) UAEM-UNAM Universidad Autónoma del Estado de México Unidad San Cayetano Toluca de Lerdo México Departamento de Química Orgánica Facultad de Química Universidad Autónoma del Estado de México Paseo Colón/Paseo Tollocan s/n Toluca Estado de México México Department de Chimie et Biochimie Université de Moncton Moncton Canadá

Reaction of ethyl (Z)-3-(heteroaryl/aryl)-2-((triphenyl-λ5-phosphaneylidene) amino) acrylates intermediates with 2,3-thiophenedicarboxaldehyde was used in novel Tandem three consecutive reactions: aza-Wittig, imine condensation and electrophilic heteroaromatic cyclization to obtain a series of indolizines. A tentative mechanism of this reaction is proposed.

关键词： iminophosphorane Tandem Reaction Indolizine Synthesis