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.

Cycloadditionen, XXII [1]. Synthese und thermische Reaktion von S-(Alkyl/Aryl)- 2.3-butadienthiosäure-estern / Cycloadditions, XXII [1]. Synthesis and Thermal Reaction of S-(Alkyl/Aryl)-2,3-butadienethioates

1994 ◽  
Vol 49 (4) ◽  
pp. 542-550 ◽  
Author(s):  
Gerhard Himbert ◽  
Dieter Fink
Keyword(s):  
Alder Reaction ◽  
Thermal Reaction ◽  
Diels Alder ◽  
Alkyl Aryl ◽  
Diels Alder Reaction ◽  
Ester Moiety ◽  
Derivatives Of

While the S-alkyl- or S-phenyl-2,3-butadienethioates 4 a-c are synthesized via the usual “Wittig ylide way”, the corresponding 2-methyl-2,3-butadienethioates 9 a-d and the 2-methyl-4.4-diphenyl-2,3-butadienethioates 9 e,f are obtained by condensation of the allenic acids 7 a,b with the thiols and thiophenols 8 in the presence of dicyclohexylcarbodiimide (DCC) and a catalytic am ount of 4-dimethylaminopyridine (DMAP). In contrast to N- or O-phenyl 2,3- butadienamides or -esters, resp., the phenyl derivatives of 4 and 9 do not undergo the intram olecular Diels-Alder reaction, but by heating, all representatives of 4 only decompose, while 9 a-d and 9 e,f rearrange to 3-alkyl(aryl)thio-2-cyclobuten-1-ones 12a-d and to 3-arylthio- 1-naphthols 14a, b, resp. Heating of the cyclobutenone 12d in the presence of N-methylaniline furnishes the 2-butenanilide 16. On reacting 1-phenylthio-1-propyne 17 with diphenylketene 18, the diphenylacetate 19 is isolated, where the naphthol derivative 14a represents the ester moiety.

An examination of VANOL, VAPOL, and VAPOL derivatives as ligands for asymmetric catalytic Diels–Alder reactions

2006 ◽  
Vol 84 (10) ◽  
pp. 1487-1503 ◽  
Author(s):  
Douglas P Heller ◽  
Daniel R Goldberg ◽  
Hongqiao Wu ◽  
William D Wulff
Keyword(s):  
Asymmetric Catalysis ◽  
Methyl Acrylate ◽  
Lewis Acids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Asymmetric Catalytic ◽  
Diels Alder Reaction ◽  
Positive Cooperativity ◽  
Derivatives Of ◽  
Methyl Phenyl

Several derivatives of the vaulted biaryl ligand VAPOL were prepared and evaluated as chiral ligands for aluminum Lewis acids in the catalytic asymmetric Diels–Alder reactions of methyl acrylate and methacrolein with cyclopentadiene. The substituents on VAPOL were introduced into the 6- and 6′-positions in an effort to further extend the chiral pocket of the major groove, which contains the phenol functions at the 4- and 4′-positions. The set of four new ligands that have been prepared have the following groups introduced into the 6- and 6′-positions of VAPOL: bromide, methyl, phenyl and 3,5-di-t-butylphenyl. All of these ligands give lower asymmetric inductions than the unsubstituted VAPOL for the Diels–Alder reactions of both methyl acrylate and methacrolein. The positive cooperativity of added carbonyl compounds on the autoinduction in the Diels–Alder reaction of methyl acrylate and cyclopentadiene were also investigated with the VANOL and VAPOL ligands as well as the 6,6′-dibromo and 6,6′-diphenyl derivatives of VAPOL. Only the reaction with VAPOL showed any significant positive cooperativity. The reaction with VANOL was sluggish at –78 °C, but at higher temperatures, the reaction did exhibit positive cooperativity that was similar to that of VAPOL. Finally, no positive cooperativity was observed with the VAPOL ligand for the reaction of methacrolein and cyclopentadiene.Key words: Diels–Alder, asymmetric catalysis, vaulted biaryl ligands, VANOL, VAPOL.

scholarly journals One-Pot Synthesis of 5,6-Dihydro-4H-1,2-Oxazines by Cyclization of Ketoximes with Derivatives of Allylbenzene

2010 ◽  
Vol 6 (1) ◽  
pp. 884-890
Author(s):  
Raad Kasim Yahya ◽  
K. M. Lokanatha Rai ◽  
Ebraheem Abdu Musad ◽  
P. T. Sowmya
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
One Pot Synthesis ◽  
Diels Alder Reaction ◽  
Chloramine T ◽  
Derivatives Of

A new series of 5,6-dihydro-4H-1,2-oxazines were synthesized via hetero Diels-Alder reaction of  α-nitrosolefins with derivatives of allylbenzene. α-Nitrosoolefins were generated from ketoximes by the action of chloramine-T and triethylamine.

scholarly journals Synthesis of dibenzosuberenone-based novel polycyclic π-conjugated dihydropyridazines, pyridazines and pyrroles

2021 ◽  
Vol 17 ◽  
pp. 719-729
Author(s):  
Ramazan Koçak ◽  
Arif Daştan
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Cycloaddition Reactions ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Reductive Treatment ◽  
High Yields ◽  
Derivatives Of ◽  
Electron Demand

The synthesis of novel polycyclic π-conjugated dihydropyridazines, pyridazines, and pyrroles was studied. Dihydropyridazine dyes were synthesized by inverse electron-demand Diels–Alder cycloaddition reactions between a dibenzosuberenone and tetrazines that bear various substituents. The pyridazines were synthesized in high yields by oxidation of dihydropyridazine-appended dibenzosuberenones with PIFA or NO. p-Quinone derivatives of pyridazines were also obtained by H-shift isomerization following the inverse electron-demand Diels–Alder reaction of tetrazines with p-quinone dibenzosuberenone. Then these pyridazines were converted to the corresponding pyrroles by reductive treatment with zinc. It was observed that all the dihydropyridazines obtained gave absorbance and emission at long wavelengths.

Design and synthesis of tetraazachlorins, tetraazabacteriochlorins and tetraazaisobacteriochlorins

2009 ◽  
Vol 13 (02) ◽  
pp. 188-202 ◽  
Author(s):  
Elena A. Makarova ◽  
Evgeny A. Lukyanets
Keyword(s):  
Dicarboxylic Acids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Azomethine Ylides ◽  
Addition Reactions ◽  
Dipolar Cycloadditions ◽  
Design And Synthesis ◽  
Diels Alder Reaction ◽  
Oxidation Resistant ◽  
Derivatives Of

Three approaches to the synthesis of reduced derivatives of tetraazaporphine such as tetraazachlorin, tetraazabacteriochlorin, and tetraazaisobacteriochlorin are reviewed. The first synthesis of alkyl-substituted tetraazachlorins was achieved by the catalytic hydrogenation of magnesium complexes of tetraazaporphines. Two other synthesis approaches for reduced tetraazaporphines based on the mixed condensation of the precursors with different hydrogenation levels and β–β addition reactions have been developed in the last decade. The use of tetramethylsuccinonitrile as the saturated component in the mixed condensation with derivatives of aromatic and heteroaromatic dicarboxylic acids enable the synthesis of oxidation-resistant benzo-; 1,2- and 2,3-naphtho-; pyrazino-; 2,3- and 3,4-pyridino-fused tetraazachlorins, tetraazabacteriochlorins, and tetraazaisobacteriochlorins. Fullerene conjugates of reduced tetraazaporphine derivatives were obtained using 1,2-dicyanofullerene as the source of the hydrogenated sites. Tetraazaporphine can act as dienophile in Diels-Alder reaction with dienes of the anthracene and cyclopentadiene series and also as dipolarophile in 1,3-dipolar cycloadditions with azomethine ylides and nitrones. In addition, the effect of the reduction of peripheral double bonds in tetraazaporphine macrocycle alone, and in combination with annelation of benzene or heterocyclic rings on the absorption spectra is discussed.

ChemInform Abstract: DIELS-ALDER REACTION OF TWO DERIVATIVES OF 3-OXOTHIOPHANES. STRUCTURE AND CONFIGURATION OF THE ADDUCT

1977 ◽  
Vol 8 (17) ◽  
pp. no-no
Author(s):  
S. D. MIKHNO ◽  
T. M. FILIPPOVA ◽  
N. S. KULACHKINA ◽  
S. I. PERETOKINA ◽  
V. I. SEREDENKO ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Derivatives Of

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).

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