Five-membered oxaza heterocyclic compounds on the basis of epoxides and aziridines

Kas’yan, L. I.; Пальчиков, В. А.; Bondarenko, Ya. S.

doi:10.1134/s1070428011060017

Cited by 18 publications

(3 citation statements)

References 225 publications

(248 reference statements)

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“…For instance, polymers of N -oxiranylmethylcarbazole are employed for recording and transmitting information. They are also used in devices that convert solar radiation energy into electrical one (solar photocells) and as photocapacitors [ 1 , 2 , 3 , 4 , 5 , 6 , 7 ]. Optical properties and film-forming ability of isolated carbazole molecules (photoluminescence maxima at 352 and 368 nm), compositions of low molecular weight epoxy resin Ruetapox 0162 with various amounts of 9-(2,3-epoxypropyl)carbazole and cured with isophoronediamine, can be exploited in LED fabrication [ 8 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Functional Polyesters N-(2,3-epoxypropyl)-4,5,6,7-tetrahydroindole by Anionic Ring-Opening Polymerization

Маркова

Emel’yanov²,

Tatarinova³

et al. 2022

Polymers

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The functional polyethers of N-(2,3-epoxypropyl)-4,5,6,7-tetrahydroindole (in up to 61% yield, Mw = 8.7–11.7 kDa) and copolymers with ethylene glycol methylglycidyl ether (Mw = 5.6–14.2 kDa) and ethylene glycol vinylglycidyl ether (Mw = 6.4–12.3 kDa) have been synthesized via anionic ring-opening polymerization in the presence of KOH without solvent. The polymerization involves the opening of the epoxy ring to deliver the linear polyethers bearing free tetrahydroindole rings and oxyethylene or vinyloxy groups in the side chain. The polyethers are soluble in ethanol, benzene, chloroform, dioxane, DMF, and DMSO. The polyethers obtained exhibit the properties of high-resistance organic semiconductors: their electrical conductivity reaches 10−14 S/cm.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Functional Polyesters N-(2,3-epoxypropyl)-4,5,6,7-tetrahydroindole by Anionic Ring-Opening Polymerization

Маркова

Emel’yanov²,

Tatarinova³

et al. 2022

Polymers

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“…These reactions are very important for the synthesis of heterocycles, and they would require a dedicated chapter to be described in details. As this chemistry has already been described in several reviews, [112][113][114][115][116] we will present only a few seminal studies and concentrate more on other transformations, which have been less in the focus of attention.…”

Section: Reactions With Epoxidesmentioning

confidence: 99%

Synthesis of Saturated Heterocycles via Metal-Catalyzed Formal Cycloaddition Reactions That Generate a C–N or C–O Bond

Waser

2013

Topics in Heterocyclic Chemistry

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In this section, the synthesis of saturated N-and O-heterocycles via formal cycloaddition is presented. The main focus is on metal-catalyzed reactions involving C-C or C-X  bond cleavage in three-or four-membered rings. After a fast presentation of pioneering works, the important breakthroughs of the last two decades are presented. The section starts with reactions involving three-membered rings. Formal [3+2] cycloadditions of donor-acceptor-substituted cyclopropanes and methylenecyclopropanes with carbonyls and imines are important methods to access tetrahydrofuran and pyrrolidine heterocycles. Formal [3+3] cycloadditions have emerged more recently. On the other hand, reactions of epoxides and aziridines with carbon monoxide or cumulenes are now well-established method to access heterocycles. These processes have been completed more recently with cycloaddition with olefins, carbonyls and imines. The section ends with the emerging field of four-membered ring activation for cycloaddition with  systems. This is the peer reviewed version of the following article: Top. Heterocycl. Chem. 2013, 32, 225, which The discovery of classical cycloaddition reactions, such as the (hetero) DielsAlder and 1,3-dipolar cycloadditions, has contributed tremendously to a more efficient access towards both carbocycles and heterocycles. The introduction of the term cycloaddition was necessary to distinguish these new types of reactions from previously discovered processes leading to cyclic structures, such as the famous Robinson annulation. In principle, each cycloaddition can be considered as a special case of the more general annulation process, but from which point on an annulation can be called a cycloaddition has been the topic of intensive discussions for decades, and is still not settled today. In 1968, Huisgen proposed a set of rules for the definition of cycloaddition, and the two first are still largely recognized as prerequisite: Although the rule that all the atoms of the starting materials have to be included in the product is not explicitly included in the definition, this requirement is usually recognized by most organic chemists. Even if electrocyclic cyclization processes were included in the original definition of Huisgen, the term cycloaddition is mostly used today for those reactions proceeding via the formation of at least two new bonds. Nevertheless, several researchers think that the term cycloaddition should be more strictly limited to reactions involving a continuous overlap of  electrons, and consequently allowing a concerted process. In fact, in his seminal publication, Huisgen already introduced further rules, in particular rule number 3, which explicitly stated that cycloadditions should not involve the cleavage of sigma bonds: -Huisgen Rule 3: "Cycloadditions do not involve the cleavage of  bonds." Unfortunately, in the same publication, Huisgen also described several reactions proceeding via -bond cleavage as cycloaddition. To solve this definition dilemma, several researchers have used th...

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“…11,12 Under these circumstances, the direct synthesis of 2-oxazolidinones from CO 2 and b-aminoalcohols [13][14][15] or aziridines [16][17][18][19] is preferable from environmental and economical viewpoints, however, some stoichiometrically consumed dehydrating reagents and high pressure or high temperature are required in most of these works. Since epoxides are known to produce ring-opened addition products with nucleophilic reagents, 20 another nonphosgene route for 2-oxazolidinones synthesis is the reaction between epoxides and carbamates, and then intramolecular cyclization to give the expected 2-oxazolidinones, [21][22][23] Scheme 1. Several alkaline agents, 23,24 such as triethylamine, have been reported as catalysts for the 2-oxazolidinones synthesis from epoxides and carbamates.…”

mentioning

confidence: 99%

Efficient synthesis of 2-oxazolidinones from epoxides and carbamates catalyzed by amine-functionalized ionic liquids

Shang

et al. 2015

RSC Adv.

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COMMUNICATION This journal isA series of amine-functionalized ionic liquids were prepared and their catalytic performance were tested in the synthesis 2-oxazodinones from epoxides and carbamates. Under optimized reaction conditions, good to excellent yields of various 2-oxazolidinones were achieved with different epoxides and carbamates. Moreoveer, the amine-functionalized ionic liquid catalyst could be easily recovered and reused without significantly loss in activity.

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Five-membered oxaza heterocyclic compounds on the basis of epoxides and aziridines

Cited by 18 publications

References 225 publications

Synthesis of Functional Polyesters N-(2,3-epoxypropyl)-4,5,6,7-tetrahydroindole by Anionic Ring-Opening Polymerization

Synthesis of Functional Polyesters N-(2,3-epoxypropyl)-4,5,6,7-tetrahydroindole by Anionic Ring-Opening Polymerization

Synthesis of Saturated Heterocycles via Metal-Catalyzed Formal Cycloaddition Reactions That Generate a C–N or C–O Bond

Efficient synthesis of 2-oxazolidinones from epoxides and carbamates catalyzed by amine-functionalized ionic liquids

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