A Synthesis of Novel Perinaphthenones from Acetylenic Esters and Acenaphthoquinone–Malononitrile Adduct in the Presence of Triphenylphosphine

Synlett ◽  
2018 ◽  
Vol 29 (15) ◽  
pp. 2011-2014
Author(s):  
Issa Yavari ◽  
Aliyeh Khajeh-Khezri ◽  
Mohammad Halvagar
Keyword(s):  
Knoevenagel Condensation ◽  
Condensation Product ◽  
Ethyl Cyanoacetate ◽  
Selective Synthesis ◽  
Atom Economy ◽  
Acetylenic Esters ◽  
X Ray ◽  
X Ray Crystallography ◽  
Catalytic Role ◽  
High Yields

A facile protocol involving Tebby zwitterions (PPh3-acetylenic esters) and the Knoevenagel condensation product of acenaphthylene-1,2-dione with malononitrile or ethyl cyanoacetate for the selective synthesis of a new series of perinaphthenone derivatives is described. Triphenylphosphine plays a catalytic role in these transformations. The structure of a typical product was confirmed by X-ray crystallography. The merits of this method include high yields of products, good atom economy, and a metal-free catalyst.

scholarly journals Silylated gallium and indium chalcogenide ring systems as potential precursors to ME (E=O, S) materials

2013 ◽  
Vol 11 (7) ◽  
pp. 1225-1238
Author(s):  
Iliana Medina-Ramírez ◽  
Cynthia Floyd ◽  
Joel Mague ◽  
Mark Fink
Keyword(s):  
Thermal Decomposition ◽  
Room Temperature ◽  
Membered Ring ◽  
Molecular Structures ◽  
Nmr Studies ◽  
X Ray ◽  
X Ray Crystallography ◽  
High Yields ◽  
Vt Nmr ◽  
State 1

AbstractThe reaction of R3M (M=Ga, In) with HESiR′3 (E=O, S; R′3=Ph3, iPr3, Et3, tBuMe2) leads to the formation of (Me2GaOSiPh3)2(1); (Me2GaOSitBuMe2)2(2); (Me2GaOSiEt3)2(3); (Me2InOSiPh3)2(4); (Me2InOSitBuMe2)2(5); (Me2InOSiEt3)2(6); (Me2GaSSiPh3)2(7); (Et2GaSSiPh3)2(8); (Me2GaSSiiPr3)2(9); (Et2GaSSiiPr3)2(10); (Me2InSSiPh3)3(11); (Me2InSSiiPr3)n(12), in high yields at room temperature. The compounds have been characterized by multinuclear NMR and in most cases by X-ray crystallography. The molecular structures of (1), (4), (7) and (8) have been determined. Compounds (3), (6) and (10) are liquids at room temperature. In the solid state, (1), (4), (7) and (9) are dimers with central core of the dimer being composed of a M2E2 four-membered ring. VT-NMR studies of (7) show facile redistribution between four- and six-membered rings in solution. The thermal decomposition of (1)–(12) was examined by TGA and range from 200 to 350°C. Bulk pyrolysis of (1) and (2) led to the formation of Ga2O3; (4) and (5) In metal; (7)–(10) GaS and (11)–(12) InS powders, respectively.

scholarly journals Cellulose sulphuric acid as a biodegradable and reusable catalyst for the Knoevenagel condensation

2010 ◽  
Vol 8 (1) ◽  
pp. 12-18 ◽  
Author(s):  
Kiran Shelke ◽  
Suryakant Sapkal ◽  
Kirti Niralwad ◽  
Bapurao Shingate ◽  
Murlidhar Shingare
Keyword(s):  
Sulphuric Acid ◽  
Knoevenagel Condensation ◽  
Ethyl Cyanoacetate ◽  
Reaction Times ◽  
Significant Loss ◽  
Reusable Catalyst ◽  
Environmental Friendliness ◽  
Solvent Free Condition ◽  
High Yields ◽  
Work Up

AbstractA green, mild and efficient method for Knoevenagel condensation of 3-formylchromone/2-chlroquinoline-3-carbaldehyde with active methylene compounds such as Meldrum’s acid/ethyl cyanoacetate using biosupported cellulose sulphuric acid (CSA) in the solid-state by grinding under solvent-free condition has been developed. This method provides several advantages including environmental friendliness, shor t reaction times, high yields and a simple work-up procedure. Moreover, the CSA was successfully reused for four cycles without significant loss of activity.

Heterometallische Cluster durch ligandunterstützte Metallfragmentkondensation / Heterometallic Clusters by Ligand Assisted Metal Fragment Condensation

1991 ◽  
Vol 46 (9) ◽  
pp. 1169-1176 ◽  
Author(s):  
Wolfgang Rohde ◽  
Gert Fendesak
Keyword(s):  
Double Bond ◽  
Chelate Complexes ◽  
Heterometallic Clusters ◽  
X Ray ◽  
X Ray Crystallography ◽  
Inert Solvent ◽  
Fragment Condensation ◽  
Olefinic Double Bond ◽  
High Yields ◽  
Iron Fragment

Dicobalt complexes of 3-vinylpropargylic alcohol derivatives react with biscyclooctenetricarbonyliron to give new chelate complexes of the iron tricarbonyl fragment with the olefinic double bond and the alcohol oxygen atom bound to the iron fragment. These compounds react upon heating in an inert solvent to give FeCo-alkynyl cluster complexes in high yields. One of these compounds has been structurally characterized by X-ray crystallography.

scholarly journals Neue Synthesewege zu neutralen gemischtsubstituierten Eisen-Schwefel-Clustern / Novel Synthetic Pathways to Neutral Mixed-Ligand Iron-Sulfur Clusters

1996 ◽  
Vol 51 (7) ◽  
pp. 1040-1048 ◽  
Author(s):  
M. Harmjanz ◽  
C. Junghans ◽  
U.-A. Opitz ◽  
B. Bahlmann ◽  
S. Pohl
Keyword(s):  
Elemental Sulfur ◽  
Large Excess ◽  
Iron Sulfur Clusters ◽  
Thiourea Derivatives ◽  
X Ray ◽  
X Ray Crystallography ◽  
Iron Sulfur ◽  
Neutral Ligands ◽  
High Yields ◽  
Sulfur Donor

The reaction of [Fe(NiSiMe3)2)2] with thiols RSH, elemental sulfur, and neutral ligands L (with sulfur donor atoms, e. g. thiourea derivatives) gives [Fe4S4(SR)2L2] clusters in high yields. The structure of [Fe4S4(2.4.6-(C3H7)3C6H2-S)2(dpdmi)2] (dpdmi: diisopropyldimethyl- imidazolthion) was determined by X-ray crystallography.When [Fe4S4I4]2- is reacted with a large excess of PMePh2 or PMe2Ph [F6S6I2(PMePh2)4] and [Fe6S6l2(PMe2Ph)4]. respectively, are obtained in nearly quantitative yield. Basket-like structures of the [Fe6S6]2+ cores were detected by X-ray structure analysis. While [Fe4S4(SR)4]2- clusters do not react with phosphanes at ambient temperature 2:2 functional­ized species like [Fe4S4(SR)2(tmtu)2] lead to basket-type clusters [Fe6S6(SR)2(PR3)4].

Activation of C–Cl Bonds: Synthesis and Structural Characterization of [Ru2(μ-Cl)(μ-PtBu2)(μ- Ph2PN(H)PPh2)(CO)4]

2013 ◽  
Vol 68 (5-6) ◽  
pp. 743-746 ◽  
Author(s):  
Tobias Mayer ◽  
Hans-Christian Böttcher
Keyword(s):  
Carbon Tetrachloride ◽  
Single Crystals ◽  
Structural Characterization ◽  
Title Compound ◽  
X Ray ◽  
X Ray Crystallography ◽  
High Yields

The synthesis and structural characterization of the complex [Ru2(μ-Cl)(μ-PtBu2)(μ-dppa)(CO)4] (4, dppa = Ph2PN(H)PPh2) are reported. The title compound and two other related complexes were obtained in high yields by the reaction of the coordinatively unsaturated species [Ru2(μ-H)(μ-PtBu2)(μ-PˆP)(CO)4] (PˆP = dppa, 3; PˆP =Ph2PN(Ph)PPh2, 5; PˆP =Ph2PN(CH2Ph)PPh2, 6) with carbon tetrachloride. Single crystals of 4 grown from dichloromethane-acetone have been analyzed by X-ray crystallography

Nano ZrO2: an efficient, recyclable, and inexpensive catalyst for diastereoselective three-component Mannich reactions

2014 ◽  
Vol 92 (7) ◽  
pp. 659-664 ◽  
Author(s):  
M. Saeed Abaee ◽  
Elahe Akbarzadeh ◽  
Abbas Shockravi ◽  
Mohammad M. Mojtahedi ◽  
Hamid Reza Khavasi
Keyword(s):  
Spectroscopic Data ◽  
Room Temperature ◽  
Aromatic Aldehydes ◽  
Significant Loss ◽  
Mannich Reactions ◽  
X Ray ◽  
X Ray Crystallography ◽  
Aniline Derivatives ◽  
High Yields ◽  
Acyclic Ketones

A facile procedure is developed for the three-component Mannich reactions of several heterocyclic, homocyclic, and acyclic ketones by using catalytic quantities of nano ZrO2. As a result, the starting ketones undergo rapid reactions with a variety of aromatic aldehydes and aniline derivatives at room temperature to produce stereoselectively high yields of the corresponding anti β-amino ketones. Interestingly, the catalyst could be recycled for several runs in a row without significant loss of its activity. The structure of the products was assigned based on their spectroscopic data and the anti stereoselectivity was confirmed by X-ray crystallography.

Synthesis With Chelated Imino Carboxylates: The Influence of Chelate Coligands on Reaction Pathways

1993 ◽  
Vol 46 (10) ◽  
pp. 1557 ◽  
Author(s):  
KJ Drok ◽  
JM Harrowfield ◽  
SJ Mcniven ◽  
AM Sargeson ◽  
BW Skelton ◽  
...  
Keyword(s):  
Ethyl Cyanoacetate ◽  
Reaction Pathways ◽  
Preliminary Evaluation ◽  
X Ray ◽  
X Ray Crystallography ◽  
Stereoselective Addition ◽  
Equilibrium Control ◽  
Synthetic Utility ◽  
Structure Determinations ◽  
Complex Ion

Synthesis and X-ray crystallography have been used to explore the chemistry of chelates derived from the imines of pyruvic and phenylpyruvic acids held in a chiral environment on cobalt(III) as [Co(en)2(HNC(CH3)CO2)]2+ (en = ethane-1,2-diamine) and [Co(en)2(HNC(CH2C6H5)CO2)]2+. The latter complex was obtained by an especially facile dehydration of the corresponding β-phenylserine complex. Significant differences in both stereo- and regio-selectivity were detected in reactions of the two complexes, and, for the reaction of butenone with [Co(en)2(HNC(CH3)CO2)]2+, a pathway indetectable in previously studied reactions of the tetraammine analogue, and leading to a chelate of 4-methyl-5,6-dihydropyridine-2-carboxylate, was observed to be dominant. Kinetically determined stereospecificity was evident in the addition of ethyl cyanoacetate to [Co(en)2(HNC(CH3)CO2)]2+, whereas equilibrium control appears to exist in the stereoselective addition of nitromethane to both complexes. Crystal structure determinations on five new complexes have been used to establish these points and other important aspects of the chemical syntheses. A considerable number of new imino and amino acids can be derived through the reactions described, and the synthetic utility of both the tetraammine and bis ( ethanediamine ) complex ion systems in providing the 'free' organic products has been subjected to preliminary evaluation through the isolation of t- leucine , N-methyl-2-phenylglycine, 2-aminomethylalanine, and some vinylglycine derivatives.

Synthesis of cyclohexapyrrolizidines: C-methylation of vinylogous amides

1978 ◽  
Vol 56 (3) ◽  
pp. 320-325 ◽  
Author(s):  
Ronald B. Kelly ◽  
Sandra J. Alward
Keyword(s):  
Convenient Method ◽  
X Ray ◽  
X Ray Crystallography ◽  
Vinylogous Amides ◽  
High Yields

A synthesis of the cyclohexapyrrolizidines 32 and 33 is described; the structure of the latter was determined by X-ray crystallography. It is anticipated that this synthesis will serve as a model for the construction of a similar pyrrolizidine system during a projected synthesis of thelepogine 2.A convenient method for the C-methylation of cyclic vinylogous amides is also described. This procedure, which is similar to published procedures, affords high yields of methylated product and is regiospecific.

scholarly journals Efficient Preparation of Potassium Arylmethylene-4-(1H-Pyrazol-5-ol)-4′-(1H-Pyrazol-5-Olate) Derivatives via a Four-Component Reaction

2018 ◽  
Vol 42 (6) ◽  
pp. 313-316
Author(s):  
Ting Wang ◽  
Yang Yu ◽  
Xushun Qing ◽  
Chenlu Dai ◽  
Cunde Wang
Keyword(s):  
Potassium Carbonate ◽  
Reaction Conditions ◽  
X Ray ◽  
X Ray Crystallography ◽  
Broad Scope ◽  
Substituted Benzaldehydes ◽  
High Yields ◽  
Operational Simplicity

A four-component reaction was investigated to prepare potassium arylmethylene-4-(1 H-pyrazol-5-ol)-4′-(1 H-pyrazol-5-olate) derivatives from dialkyl but-2-ynedioates, phenylhydrazine, substituted benzaldehydes and potassium carbonate without any catalyst or promoter. The structure of a typical product was confirmed by X-ray crystallography. The advantages of the present methodology are efficiency, broad scope, operational simplicity, high yields and mild reaction conditions.

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