4-Phenyl-1,2,4-triazoline-3,5-dione in organic synthesis (review)

Korobitsyna, I. K.; Khalikova, A. V.; Rodina, L. L.; Shusherina, N. P.

doi:10.1007/bf00506417

Cited by 17 publications

(25 citation statements)

References 147 publications

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“…[26] To prevent these side reactions, the studies must be carried out in the absence of light and under anhydrous conditions. [26] To prevent these side reactions, the studies must be carried out in the absence of light and under anhydrous conditions.…”

Section: Resultsmentioning

confidence: 99%

Dynamic Covalent Chemistry: A Facile Room‐Temperature, Reversible, Diels–Alder Reaction between Anthracene Derivatives and N‐Phenyltriazolinedione

Roy

Lehn

2011

Chemistry An Asian Journal

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A series of readily accessible, dynamic Diels-Alder reactions that are reversible at room temperature have been developed between anthracene derivatives as dienes and N-phenyl-1,2,4-triazoline-3,5-dione as the dienophile. The adducts formed undergo reversible component exchange to form dynamic libraries of equilibrating cycloadducts. Furthermore, reversible adduct formation allows temperature-dependent modulation of the fluorescent properties of anthracene components; a feature of potential interest for the design of optodynamic polymeric materials by careful selection and manipulation of these simple dienes and dienophiles.

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Section: Resultsmentioning

confidence: 99%

Dynamic Covalent Chemistry: A Facile Room‐Temperature, Reversible, Diels–Alder Reaction between Anthracene Derivatives and N‐Phenyltriazolinedione

Roy

Lehn

2011

Chemistry An Asian Journal

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“…[37] As such, they should be able to undergo a sequential Diels-Alder reaction, a so-called transmissive cycloaddition. [38] To test this possibility, the triene 42 was treated with the very reactive dienophile N-phenyltriazoline-3,5-dione (PTAD), [39] in situ prepared by oxidation of the urazole 68 with lead tetraacetate in dichloromethane at -10°C. The conversion of 42 was complete within 10 min, and chromatography gave the pentacyclic compound 69 as a single diastereomer in 81 % yield.…”

Section: Discussion and Outlookmentioning

confidence: 99%

Intramolecular Heck Couplings and Cycloisomerizations of Bromodienes and Enynes with 1′,1′‐Disubstituted Methylenecyclopropane Terminators: Efficient Syntheses of [3]Dendralenes

et al. 2005

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2-Bromoalka-1,n-dienes such as 9, 30 and 14 (n = 7) with tetrasubstituted methylenecyclopropane end groups, under palladium catalysis, underwent cyclization with cyclopropane-ring opening to give 2-ethenyl-3-methylene-1-cycloalkenes 41 (n = 6), 42 (n = 7), and 43, which are substituted monocyclic [3]dendralenes, in 65, 63 and 70 % yield, respectively. The same cross-conjugated trienes were isolated in good to excellent yields (77-92 %) from the corresponding 1,6-(10-H, 15) and 1,7-enynes (28-H) by a more atom-economic, palladium-catalyzed cycloisomerization. The vinylpalladium halide intermediate generated by initial carbopalladation of the 1,6-enyne 10-H with in situ generated phenylpalladium iodide also underwent the same cyclization cascade

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“…There are some papers dealing with the study of behavior of 4‐substituted 1,2,4‐triazoline‐3,5‐dione (TAD) in thermal and photochemical [4 + 2]‐, [3 + 2]‐, [2 + 2]‐cycloaddition, ene and curing reactions . An extensive study of the products structure, the reaction rate and the solvent effect on the reaction of [4 + 2]‐cycloaddition of 1 with various 1,3‐dienes was presented . Practically, at the same time, the ene synthesis of 1 with various alkenes was initiated .…”

Section: Introductionmentioning

confidence: 99%

“…An extensive study of the products structure, the reaction rate and the solvent effect on the reaction of [4 + 2]‐cycloaddition of 1 with various 1,3‐dienes was presented . Practically, at the same time, the ene synthesis of 1 with various alkenes was initiated . N ‐allylurazole derivatives, the ene reaction products, are usually formed when the allyl hydrogen atom is present in alkene as well as α‐shift of the double bond in the product is possible …”

Section: Introductionmentioning

confidence: 99%

4‐Phenyl‐1,2,4‐triazoline‐3,5‐dione in the ene reactions with cyclohexene, 1‐hexene and 2,3‐dimethyl‐2‐butene. The heat of reaction and the influence of temperature and pressure on the reaction rate

Kiselev

Kornilov

Kashaeva

et al. 2014

J of Physical Organic Chem

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The values of the enthalpy (53.3; 51.3; 20.0 kJ mol−1), entropy (−106; −122; −144 J mol−1K−1), and volume of activation (−29.1; −31.0; −cm3 mol−1), the reaction volume (−25.0; −26.6; −cm3 mol−1) and reaction enthalpy (−155.9; −158.2; −150.2 kJ mol−1) have been obtained for the first time for the ene reactions of 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione 1, with cyclohexene 4, 1‐hexene 6, and with 2,3‐dimethyl‐2‐butene 8, respectively. The ratio of the values of the activation volume to the reaction volume (∆V≠corr/ΔVr − n) in the ene reactions under study, 1 + 4→5 and 1 + 6→7, appeared to be the same, namely 1.16. The large negative values of the entropy and the volume of activation of studied reactions 1 + 4→ 5 and 1 + 6→7 better correspond to the cyclic structure of the activated complex at the stage determining the reaction rate. The equilibrium constants of these ene reactions can be estimated as exceeding 1018 L mol−1, and these reactions can be considered irreversible. Copyright © 2014 John Wiley & Sons, Ltd.

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4-Phenyl-1,2,4-triazoline-3,5-dione in organic synthesis (review)

Cited by 17 publications

References 147 publications

Dynamic Covalent Chemistry: A Facile Room‐Temperature, Reversible, Diels–Alder Reaction between Anthracene Derivatives and N‐Phenyltriazolinedione

Dynamic Covalent Chemistry: A Facile Room‐Temperature, Reversible, Diels–Alder Reaction between Anthracene Derivatives and N‐Phenyltriazolinedione

Intramolecular Heck Couplings and Cycloisomerizations of Bromodienes and Enynes with 1′,1′‐Disubstituted Methylenecyclopropane Terminators: Efficient Syntheses of [3]Dendralenes

4‐Phenyl‐1,2,4‐triazoline‐3,5‐dione in the ene reactions with cyclohexene, 1‐hexene and 2,3‐dimethyl‐2‐butene. The heat of reaction and the influence of temperature and pressure on the reaction rate

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