Synthèse d'aryl nitronorbornènes par cycloaddition de Diels–Alder entre les aryl-nitroéthylènes et le cyclopentadiène. Justification de la stéréochimie et de la réactivité relative observées par la méthode CNDO/II. Obtention d'aryl aminonorbornènes

1985 ◽  
Vol 63 (9) ◽  
pp. 2354-2361 ◽  
Author(s):  
Jean Bourguignon ◽  
Gilles Le Nard ◽  
Guy Queguiner
Keyword(s):  
Theoretical Calculations ◽  
Alder Reaction ◽  
Diels Alder ◽  
Relative Reactivity ◽  
H Nmr ◽  
Diels Alder Reaction

Syntheses of numerous 2-aryl nitroethylenes (nitrostyrenes) have been optimized. The nitrostyrenes have been reacted with cyclopentadiene in Diels–Alder cycloadditions and the 3-aryl 2-nitronorbornenes obtained have been reduced into 3-aryl 2-aminonorbornenes. These compounds are potentially dopaminergic molecules. The stereochemistry of the adducts obtained in the Diels–Alder reaction has been determined by 1H nmr. The stereochemistry and the relative reactivity of the nitrostyrenes versus cyclopentadiene have been confirmed by theoretical calculations based on the CNDO/II method.

scholarly journals Synthesis and Evaluation of Substituted 4,4a-Dihydro-3H,10H-pyrano[4,3-b][1]benzopyran-10-one as Antimicrobial Agent

2013 ◽  
Vol 2013 ◽  
pp. 1-11 ◽  
Author(s):  
Amanpreet Kaur ◽  
Vishal Sharma ◽  
Abhishek Budhiraja ◽  
Harpreet Kaur ◽  
Vivek Gupta ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Enol Ethers ◽  
Spectral Techniques ◽  
Mass Spectral ◽  
H Nmr ◽  
Diels Alder Reaction ◽  
Electron Withdrawing Group ◽  
Inhibitory Potential ◽  
C Nmr

A series of pyrano[4,3-b][1]benzopyranones (7a–t) were synthesized through hetero-Diels-Alder reaction of substituted 3-formylchromones (5) with enol ethers (6), characterized by IR, 1H NMR, 13C NMR, and mass spectral techniques. All the compounds were evaluated for antimicrobial activity against various bacterial and fungal strains, found to possess significant inhibitory potential, particularly, compounds bearing electron withdrawing group -fluoro such as 7i and 7h. Compounds were also tested and displayed a significant inhibitory potential against methicillin-resistant Staphylococcus aureus (MRSA).

New synthesis of tetraazachlorins and tetraazabacteriochlorins by Diels–Alder reaction of tetraazaporphine

2000 ◽  
Vol 04 (05) ◽  
pp. 525-531 ◽  
Author(s):  
ELENA A. MAKAROVA ◽  
GALINA V. KOROLYOVA ◽  
OLEG L. TOK ◽  
EVGENY A. LUKYANETS
Keyword(s):  
Electronic Absorption Spectra ◽  
Analysis Data ◽  
Alder Reaction ◽  
Diels Alder ◽  
Elemental Analysis Data ◽  
Tert Butyl ◽  
H Nmr ◽  
Diels Alder Reaction ◽  
Cis And Trans Isomers ◽  
Cis And Trans

The use of the Diels–Alder reaction of unsubstituted tetraazaporphine as dienophile with some dienes of the anthracene series for the synthesis of novel substituted tetraazachlorins, tetraazabacteriochlorins and tetraazaisobacteriochlorins is reported. The condensation of tetraazaporphine with anthracene, 9,10-dimethyl- or 2,6-di(tert-butyl)anthracene in boiling chlorobenzene gives novel dibenzobarreleno-substituted tetraazachlorins 3–5 in yields of up to 71%. When AlCl3 was used as catalyst in the reaction of tetraazaporphine with 2,6-di(tert-butyl) anthracene, the corresponding cis- and trans-dibenzobarreleno-substituted tetraazabacteriochlorins 6a and 6b were obtained. The reaction of tetraazaporphine with the more active diene 2,3-benzanthracene at 130°C gives mainly benzonaphtho[2,3-b]barreleno-substituted tetraazachlorin 7, while the same reaction conducted at 220°C led to a mixture of cis- and trans isomers of tetraazabacteriochlorins 8a and 8b and tetraazaisobacteriochlorins 9a and 9b. The products were characterized using elemental analysis data and mass, 1H NMR and visible spectra. The effect of hydrogenation of one or two double bonds of the tetraazaporphine macrocycle on the electronic absorption spectra is discussed.

scholarly journals The evaluation of chemoselectivity in multicomponent domino Knoevenagel/Diels-Alder reaction: A DFT study

2021 ◽  
pp. 66-66
Author(s):  
Mina Attarbashi ◽  
Shiraz Zabarjad ◽  
Marjaneh Samadizadeh
Keyword(s):  
Theoretical Calculations ◽  
Alder Reaction ◽  
Diels Alder ◽  
Acid Base ◽  
Bond Rotation ◽  
Solvent Phase ◽  
Diels Alder Reaction ◽  
Meldrum Acid ◽  
Predominant Product ◽  
Clear Information

Herein, the chemoselectivity of the multicomponent domino Knoevenagel/Diels-Alder reaction is investigated in terms of theoretical calculations. Structures of reagents, transition states, intermediates and products are optimized at the M062X/6-31+G(d,p) level of theory. The reaction mechanism involves processes of bond rotation, isomerization, asymmetric cycloaddition, acid-base and nucleophile-electrophile competitions, which are studied to deliver a clear information of the mechanism in terms of chemoselectivity considerations. Accordingly, the chemoselectivity of the reaction is controlled by the releasing acetone during the decomposition of Meldrum acid in the presence of methanol and L-proline (DG# = 61.45 kcal mol-1). Comparing calculated results (gas and solvent phase) with the experimental ones showed that utilizing these reagents are the kinetical favorite path for the chemoselective multicomponent cascade Knoevenagel/Diels-Alder reaction to produce the predominant product (>95 %). The results suggest that the creation of cis-spiro cyclohexanone is the predominant chemoselective product under kinetic control of the desired enone.

Imino Diels–Alder reaction — An efficient synthetic protocol for 2-methyl-4-substituted tetrahydroquinolines catalyzed by copper dipyridine dichloride

2010 ◽  
Vol 88 (5) ◽  
pp. 443-452 ◽  
Author(s):  
C. S. Kavitha ◽  
K. M. Hosamani ◽  
R. S. Harisha
Keyword(s):  
Elemental Analysis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Reusable Catalyst ◽  
Substituted Anilines ◽  
H Nmr ◽  
Diels Alder Reaction ◽  
First Time ◽  
C Nmr

For the first time, copper dipyridine dichloride (CuPy2Cl2) is used as an efficient and reusable catalyst for the imino Diels–Alder reaction of para-substituted anilines with N-vinylpyrrolidinone, N-vinylcarbazole, and N-vinylcaprolactam in acetonitrile to afford the corresponding 2-methyl-4-substituted-1,2,3,4-tetrahydroquinoline derivatives in excellent yields with good purity. The products were characterized by FTIR, 1H NMR, 13C NMR, MS, and elemental analysis.

Diels-Alder Reactions of Cyclopentadiene with Several Ferrocenyl- and η6-Phenyltricarbonylchromium Analogues of Chalcone. Catalytic Effect of SiO2

1996 ◽  
Vol 61 (3) ◽  
pp. 364-370 ◽  
Author(s):  
Monika Prokešová ◽  
Grety Rihs ◽  
Štefan Toma
Keyword(s):  
Good Yield ◽  
Room Temperature ◽  
Catalytic Effect ◽  
Alder Reaction ◽  
Diels Alder ◽  
Nmr Spectrum ◽  
X Ray ◽  
H Nmr ◽  
Diels Alder Reaction ◽  
Electron Withdrawing Group

The Diels-Alder reaction of cyclopentadiene with eight electron deficient dienophiles was studied. The reaction was performed at room temperature using silica gel as an inorganic support, without solvent. Only one of the two possible Diels-Alder adducts was isolated in moderate to good yield. The structure of products with endo-oriented electron-withdrawing group was proved by 1H NMR spectrum and in one case (9b) by X-ray analysis.

scholarly journals A DFT investigation of Diels-Alder reaction of ethyl propiolate to the cage-annulated hexacyclo[7.5.2.01,6.06,13.08,12.010,14]hexadeca-2,4-diene-7,16-dione

2018 ◽  
Vol 83 (7-8) ◽  
pp. 837-846
Author(s):  
Abdurrahman Atalay ◽  
Riza Abbasoglu
Keyword(s):  
Theoretical Calculations ◽  
Cycloaddition Reaction ◽  
Dft Method ◽  
Alder Reaction ◽  
Diels Alder ◽  
Frontier Molecular Orbital ◽  
Kinetic Control ◽  
Diels Alder Reaction ◽  
Potential Map ◽  
Good Agreement

The Diels?Alder (DA) reaction between the cage-annulated diene hexacyclo[7.5.2.01,6.06,13.08,12.010,14]hexadeca-2,4-diene-7,16-dione (HHDD) with a cyclohexa-1,3-diene moiety and ethyl propiolate (EP) dienophile was investigated by the DFT method at the B3LYP/6-31+G(d,p) level to elucidate the mechanism and regioselectivity features of the reaction. The geometrical and electronic structures of the caged diene HHDD and EP were studied at B3LYP/6-31+G(d,p) level. In order to identify facial- and regio-selectivity of the DA reaction of HHDD and EP, the frontier molecular orbital (FMO) interactions of the reactants according to the FMO theory, and the molecular electrostatic potential map of HHDD were examined. The potential energy surface (PES) of the related DA reaction was calculated, and optimizations of transition states and of products corresponding to critical points on the PES were performed at the B3LYP/6-31+G(d,p), and their configurations were determined. In addition, the thermodynamic and kinetic parameters of each possible cycloaddition reaction were calculated using the B3LYP/6-31+G(d,p) method to determine whether the reaction occurs under thermodynamic or kinetic control. The thermochemical results showed that the related DA cycloaddition proceeds under kinetic control, and the activation energies of syn cycloadditions are clearly lower than that of anti cycloadditions. The theoretical calculations are in good agreement with experimental results.

scholarly journals The Diels–Alder reaction of 4-methoxy-7-hydroxyisobenzofuran with methyl vinyl ketone; a general method for identification of some regioisomeric α-naphthols

1985 ◽  
Vol 63 (3) ◽  
pp. 735-738 ◽  
Author(s):  
B. A. Keay ◽  
R. Rodrigo
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Vinyl Ketone ◽  
Methyl Vinyl Ketone ◽  
General Phenomenon ◽  
Methyl Vinyl ◽  
H Nmr ◽  
Diels Alder Reaction ◽  
Proton Resonances ◽  
General Method

Two regioisomeric α-naphthols 14 and 15 obtained by aromatization of the methyl vinyl ketone adducts of an unsymmetrical isobenzofuran 9 are differentiated from each other by the observation of significant upfield shifts of the peri proton resonances in the 1H nmr spectra of their acetates 16 and 17. Such upfield shifts of 0.3–0.6 ppm appear to be a general phenomenon and are probably due to the anisotropic effect of the acetate carbonyl group.

scholarly journals Crystal structure of 5,7,12,14-tetrahydro-5,14:7,12-bis([1,2]benzeno)pentacene-6,13-dione

2016 ◽  
Vol 72 (12) ◽  
pp. 1734-1738 ◽  
Author(s):  
Mohammad Nozari ◽  
Jerry P. Jasinski ◽  
Manpreet Kaur ◽  
Anthony W. Addison ◽  
Ahmad Arabi Shamsabadi ◽  
...  
Keyword(s):  
High Resolution Mass Spectrometry ◽  
Alder Reaction ◽  
Diels Alder ◽  
Rotating Disc ◽  
H Nmr ◽  
Separation Membranes ◽  
Gas Separation Membranes ◽  
Diels Alder Reaction ◽  
Ft Ir ◽  
Polymers Of Intrinsic Microporosity

The lattice of 5,7,12,14-tetrahydro-5,14:7,12-bis([1,2]benzeno)pentacene-6,13-dione, C34H20O2, at 173 K has triclinic (P-1) symmetry and crystallizes with four independent half-molecules in the asymmetric unit. Each molecule is generated from a C17H10O substructure through an inversion center at the centroid of the central quinone ring, generating a wide H-shaped molecule, with a dihedral angle between the mean planes of the terminal benzene rings in each of the two symmetry-related pairs over the four molecules of 68.6 (1) (A), 65.5 (4) (B), 62.3 (9) (C), and 65.8 (8)° (D), an average of 65.6 (1)°. This compound has applications in gas-separation membranes constructed from polymers of intrinsic microporosity (PIM). The title compound is a product of a double Diels–Alder reaction between anthracene andp-benzoquinone followed by dehydrogenation. It has also been characterized by cyclic voltammetry and rotating disc electrode polarography, FT–IR, high resolution mass spectrometry, elemental analysis, and1H NMR.

Regioselective Diels–Alder reaction to open-cage ketolactam derivatives of C60

2017 ◽  
Vol 15 (29) ◽  
pp. 6136-6146 ◽  
Author(s):  
Teruhiko Tanaka ◽  
Ryuichi Nojiri ◽  
Yoshiki Sugiyama ◽  
Ryouhei Sawai ◽  
Toshikazu Takahashi ◽  
...  
Keyword(s):  
Theoretical Calculations ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Derivatives Of ◽  
C Nmr

Open-cage ketolactam fullerenes reacted with dienes on the rim of the orifice both regio- and endo-selectively, which were confirmed by 2D INADEQUATE 13C NMR of 13C enriched material/HMBC spectra as well as the theoretical calculations.

The Diels-Alder Reaction of 2-Ethenyl-1,4-Benzodioxin: A New and Simple Synthesis of Bisaryl Ethers

Synlett ◽  
1989 ◽  
Vol 1989 (01) ◽  
pp. 30-32
Author(s):  
Thomas V. Lee ◽  
Alistair J. Leigh ◽  
Christopher B. Chapleo
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Simple Synthesis ◽  
Diels Alder Reaction
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