Search results for "Cycloaddition"
showing 10 items of 392 documents
Synthesis of Highly Functionalized Fluorinated Cispentacin Derivatives
2012
Fluorinated highly functionalized cispentacin derivatives were synthetised starting from an unsaturated bicyclic b-lactam through C¼C bond functionalization via the dipolar cycloaddition of a nitrile oxide, isoxazoline opening, and fluorination by OH/F exchange.
Toward an understanding of the 1,3-dipolar cycloaddition between diphenylnitrone and a maleimide:bisamide complex. A DFT analysis of the reactivity o…
2007
Abstract The 1,3-dipolar cycloaddition between diphenylnitrone and a maleimide:bisamide complex has been studied using density functional theory (DFT) methods at the B3LYP/6-31G∗ level. The molecular recognition of the bisamide receptor to maleimide favors the formation of the complex through three hydrogen bonds. However, they are not able to produce an efficient acceleration of the cycloaddition because the symmetric substitution of the dipolarophile sites. This poor capability is discussed in base of the transition state structures and the analysis of the reactivity indexes of the reagents.
Triazole-Containing [FeFe] Hydrogenase Mimics: Synthesis and Electrocatalytic Behavior
2019
Through a Cu-catalyzed Huisgen cycloaddition between terminal alkynes and azides (CuAAC) reaction, azide [(μ-SCH2)2N(4-N3C6H4)Fe2(CO)6] has demonstrated to be a robust and versatile reagent able to...
Addition reactions of heterocycles—IV
1973
Abstract The reactivity of indole derivatives towards nitrilimines has been studied. Substituents at positions 1, 2 and 3 of the indole ring greatly affect the course of the reaction. 1,3-Dipolar cycloaddition products (3a,8a,dihydropyrazole-[3,4-b]-indole derivatives) and non-cyclic addition products (3-indolyl derivatives) were obtained depending on these substituents. The structures reported were assigned on the basis of satisfactory analytical, spectroscopic and chemical data.
ChemInform Abstract: (4 + 2) Cycloaddition of Indole Derivatives with Bismaleimides: A Route to New Biscarbazoles.
2010
Zur Regiochemie von [4 + 2]-Cycloadditionen mit Methylpyrano[3,4-b]indol-3-onen und unsymmetrischen Dienophilen
1989
Die methylierten Pyrano[3,4-b]indol-3-one 1a, 1b reagieren mit acyclischen, unsymmetrischen CC-Dienophilen nach einer Diels-Alder-Reaktion/CO2-Extrusion zu selektiv funktionalisierten Carbazolen 2. In Abhangigkeit von der Struktur der Reaktionspartner wird keine oder geringe bis hohe Regioselektivitat festgestellt. Diethylmesoxalat reagiert mit 1a, 1b regioselektiv zu neuen 2,3-difunktionalisierten Indolen 4a, 4b, die aus einer regiokontrollierten [4 + 2]-Cycloaddition und Cycloreversion resultieren, wobei Pyrano[3,4-b]indoldicarbonsaure-diethylester 3a, 3b als Intermediate auftreten durften. Regiochemistry of [4 + 2] Cycloadditions with Methylpyrano[3,4–b]indol-3-ones and Unsymmetric Dieno…
The reactivity of 2-vinylindoles with dimethyl acetylenedicarboxylate
1984
Abstract The overall rates of reaction of 1-substltuted-1- (1-methyl-2-indolyl)ethenes with dimethyl acetylenedicarboxylate are considerably lower than those of the corresponding 2-vinyl- pyrroles. Steric interaction between the N-methyl group on the indole ring and the 1-substituent on the ethenyl group prevents the diene system adopting a coplanar cisoid configuration and, thereby, inhibits the π4 + π2 cycloaddition reaction of the system with dimethyl acetylenedicarboxylate. Under such conditions, the indolylethene preferentially undergoes a Michael addition reaction at the 3-position. The π4 + π2 cycloaddition reaction is promoted at elevated temperatures. No evidence was found for a Co…
4 H ‐3,1‐Benzoxathiine aus Benzothiet und Carbonylverbindungen
1990
4H-3,1-Benzoxathiines from Benzothiete and Carbonyl Compounds The o-quinoid 8-π electron system 2, generated by thermal ring opening of benzothiete (1) undergoes [8π + 2π] cycloaddition reactions with electron-deficient carbonyl compounds 3. In accordance with the frontier orbital theory, 4H-3,1-benzoxathiines (4) are obtained in a regioselective manner.
Cycloaddition von Benzothiet an 4‐substituierte Styrole
1989
Durch thermische Ringoffnung entsteht aus Benzothiet (1) ein 8-π-Elektronensystem 2, das mit den 4-substituierten Styrolen 3a–j die Cycloaddukte 4/5a–j bildet. Die Erhohung der Reaktivitat durch elektronenspendende oder elektronenanziehende Reste und die Einflusse auf die Regioselektivitat werden an Hand von Grenzorbitalbetrachtungen diskutiert. Cycloaddition of Benzothiete of 4-Substituted Styrenes By thermal ring opening benzothiete (1) generates an 8-π electron system 2, which forms the cycloadducts 4/5a–j with 4-substituted styrenes 3a–j. The enhancement of the reactivity by electrondonating as well as electron-withdrawing substituents and their influence on the regioselectivity are dis…
Cationic Iron Aminocarbene Complexes as Dienophiles in Diels‐Alder Reaction with Cyclopentadiene
1996
The cationic iron (alkynyl)aminocarbene complexes [Cp(CO)2Fe(C(NHR)CCSiMe3][PF6], (R C6H5, p-CH3C6H4) 1 derived from aromatic amines smoothly react with cyclopentadiene in dichloromethane to yield the cycloadducts 2. No reaction was observed for complexes derived from sterically demanding aliphatic amines, like L-alanine tert-butyl ester. For comparison, the alkynyl-substituted acyl iron compounds Cp(CO)2Fe(CO)CC (R SiMe3, C6H5) 3 were investigated, requiring TiCl4 catalysis to undergo the cycloaddition reaction. The structures of the cycloadducts 4 were determined by X-ray crystallography.