Design strategy of enediynes and enyne-allenes

Maretina, I. A.

doi:10.1134/s1070363208020126

Cited by 14 publications

(10 citation statements)

References 120 publications

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“…Radical initiated reactions of phenyl-substituted arenediynes are known to preferentially result in the formation of C 1 -C 5 cyclized products known as fulvenes. 4,8 Radical initiated cyclization of compounds 1-3 was performed by the addition of Bu 3 SnH/AIBN (Scheme 3). The reaction mixture was quenched with HCl after 12 h. Compound 1 with no ortho substituents yielded the expected fulvene product 4 with an isolated yield of 40% (Scheme 3).…”

Section: Contents Lists Available At Sciencedirectmentioning

confidence: 99%

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Synthesis and reactivity of anthracenyl-substituted arenediynes

Gavvalapalli

Ren

Moore

2015

Tetrahedron Letters

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Section: Contents Lists Available At Sciencedirectmentioning

confidence: 99%

“…[1][2][3][4] Single crystals of molecules 1-3 were grown to determine the distance between alkyne groups and the preferred intramolecular orientation of anthracenyl moieties (Fig. 2).…”

Section: Contents Lists Available At Sciencedirectmentioning

confidence: 99%

Synthesis and reactivity of anthracenyl-substituted arenediynes

Gavvalapalli

Ren

Moore

2015

Tetrahedron Letters

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“…The naturally occurring enediynes have inspired chemists to make strategical use of the Bergman cyclization in synthesis where these applications ranged from the natural product synthesis of target enediynes with antibiotic, antitumor activity to the use of designer enediynes in heterocyclic synthesis, polymer chemistry, and materials science . For these purposes, the understanding of the kinetics of the Bergman cyclization and the electronic factors, which determine its barrier and the endothermicity of the reaction, is of fundamental importance.…”

Section: The Chemistry Of Enediynes and Related Compoundsmentioning

confidence: 99%

“…Nicolaou and Chen reviewed the influence of enediynes on the development of total synthesis . Maretina summarized design strategies of enediynes and enyne‐allenes stretching from organic to metallorganic chemistry . Guleskaya and Tyaglivy reviewed the use of enediynes in heterocyclic synthesis …”

Section: Introductionmentioning

confidence: 99%

Enediynes, enyne‐allenes, their reactions, and beyond

Kraka

2013

WIREs Comput Mol Sci

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Enediynes undergo a Bergman cyclization reaction to form the labile 1,4-didehydrobenzene (p-benzyne) biradical. The energetics of this reaction and the related Schreiner-Pascal reaction as well as that of the Myers-Saito and Schmittel reactions of enyne-allenes are discussed on the basis of a variety of quantum chemical and available experimental results. The computational investigation of enediynes has been beneficial for both experimentalists and theoreticians because it has led to new synthetic challenges and new computational methodologies. The accurate description of biradicals has been one of the results of this mutual fertilization. Other results have been the computer-assisted drug design of new antitumor antibiotics based on the biological activity of natural enediynes, the investigation of hetero-and metallo-enediynes, the use of enediynes in chemical synthesis and materials science, or an understanding of catalyzed enediyne reactions. C 2013 John

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“…The chemistry of high unsaturated compounds, in particular, endiine having various functional groups in molecule, is of large scientific and practical interest [1][2][3][4][5][6][7][8][9][10]. It was found out that the endiine derivatives isolated from plants and microorganisms possessed strong fungicide, antimicrobial and insecticide actions [11][12][13][14][15][16][17][18][19].…”

Section: Introductionmentioning

confidence: 99%

Investigation of Synthesis of Functionally Substituted Endiines and Their Chemical and Microbiological Conversion

Veliyev¹,

Salmanov²,

Shatirova³

et al. 2013

IJOC

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The methods of preparation of endiine and endiallene diols by interaction of cis-1,4-dibrombutene and cis-1,4-dichlorrbutene with monosubstituted acetylene alcohols in presence of the catalytic systems consisting of one-iodide copper, triethylamine and K 2 СО 3 in a medium of dimethylformamide have been developed. It has been shown that unlike 1,4-dibrombutene, the nucleophilic substitution reaction with 1,4-dichlorbutene proceeds by acetylene-allene isomerization with formation of endiallene diols. It has been established that the endiine diols can be used in thin organic synthesis (in the reactions of oxidation, splitting, dehydration, epoxidation, hydrolysis, 1,2-cycloaddition and hypochlorination) with the aim of preparation of practically useful substances. It has been revealed during hydrolysis of epoxide compounds by the chemical and microbiological methods that in the course of microbiological hydrolysis (Aspеrgillus niger), the optically active trans-structured diols are formed.

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Design strategy of enediynes and enyne-allenes

Cited by 14 publications

References 120 publications

Synthesis and reactivity of anthracenyl-substituted arenediynes

Synthesis and reactivity of anthracenyl-substituted arenediynes

Enediynes, enyne‐allenes, their reactions, and beyond

Investigation of Synthesis of Functionally Substituted Endiines and Their Chemical and Microbiological Conversion

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