13728-34-2Relevant articles and documents
o-Quinonoid heterocycles: Benzo[c]tellurophene
Morkved, Eva H.,Lakshmikantham,Cava, Michael P.
, p. 9149 - 9150 (1996)
The first synthesis of the o-quinonoid heterocycle benzo[c]tellurophene (5) has been achieved. Compound 5, prepared in two steps from the known 1,3-dihydrobenzo[c]tellurophene diiodide (6), was characterized spectroscopically, and by Diels-Alder trapping reactions.
Traceless linkers for solid-phase synthesis. Homo- and hetero-Diels-Alder reactions of o-quinodimethanes
Craig, Donald,Robson, Michael J.,Shaw, Simon J.
, p. 1381 - 1383 (1998)
The synthesis and Diels-Alder reactions of a polymer-supported o-quinodimethane are described. Reaction with dimethyl acetylenedicarboxylate, benzoquinone and trichloroacetonitrile as dienophiles gives respectively substituted naphthalenes or an isoquinoline off-resin, whilst reaction with aldehydes and imines gives polymer-supported benzodihydropyrans and tetrahydroisoquinolines. The latter heterocyclic products undergo Lewis or Br?nsted acid-mediated cleavage reactions which allow incorporation of further functionality at the point of cleavage whilst leaving no trace of attachment to the polymer support.
Palladium-catalyzed tandem Heck and aldol reactions between 2-bromobenzaldehydes and functionalized alkenes leading to naphthalenes
Cho, Chan Sik,Lim, Dong Kwon,Zhang, Jiao Qiang,Kim, Tae-Jeong,Shim, Sang Chul
, p. 5653 - 5656 (2004)
2-Bromobenzaldehydes react with an array of suitably functionalized alkenes in the presence of a catalytic amount of a palladium catalyst together with a base to afford the corresponding naphthalenes in moderate to good yields.
A 3 - amino -2 - naphthalene armor acid compound preparation process (by machine translation)
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Paragraph 0030; 0031, (2019/06/27)
The invention discloses a 3 - amino - 2 - naphthalene armor acid compound preparation process, characterized in that in the phthaldialdehyde in three is made [...] condensed under the action of the 2, 3 - naphthalene carboxylic acid dimethyl ester; the alkaline hydrolysis is under the condition of 2, 3 - naphthalene carboxylic acid mono methyl ester; then through the DPPA reaction will be carboxyl group into amino, to obtain 3 - tert-butoxy-carboxamide yl - 2 - naphthalene carboxylic acid methyl ester; finally ester, and further takes off uncle butoxycarbonyl, to obtain 3 - amino - 2 - naphthoic acid. The method of mild reaction conditions, suitable for different substrate, without the need to use high temperature autoclave equipment, reduce the safety risk in the production process, to reduce the equipment investment, energy consumption can be reduced, which is suitable for large-scale production. (by machine translation)
Gold-Catalyzed Ring Expansion of Enyne-Lactone: Generation and Transformation of 2-Oxoninonium
Luo, Kui,Cao, Tongxiang,Jiang, Huanfeng,Chen, Lianfen,Zhu, Shifa
supporting information, p. 5856 - 5859 (2017/11/10)
An efficient gold-catalyzed ring-expansion reaction of enyne-lactones to form 2-oxoninonium intermediates is reported. The 2-oxoninonium generated in this work could undergo further 6π electrocyclization and aromatization reaction to produce different aromatic compounds.
Access to polysubstituted naphthalenes and anthracenes via a retro-Diels–Alder reaction
Akin, Esra Turan,Erdogan, Musa,Dastan, Arif,Saracoglu, Nurullah
, p. 5537 - 5546 (2017/08/22)
Naphthalene and anthracene nuclei are present in several natural and synthetic compounds. Due to their unique physical and chemical properties, access to functionalized naphthalenes and anthracenes has attracted the attention of both synthetic and medicinal chemists over the decades. In this study, successive Diels–Alder/retro-Diels–Alder reactions of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate with various bicyclic alkenes in one pot to yield naphthalene and anthracene derivatives are reported. Using anti- and syn-cyclotrimers derived from the cyclotrimerization of benzobarrelene as alkene partner enabled efficient synthesis of trinaphthylene.
EPR Studies on Carboxylic Esters. Part 15. Spin Density Distribution in the Radical Anions of Naphthalenecarboxylic Esters
Strey, Karsten,Voes, Juergen
, p. 648 - 682 (2007/10/03)
Persistent radical anions of naphthalene mono-, di-, and tetracarboxylic esters are generated by in situ electroreduction.The spin density distribution is determined from the proton hfs coupling constants as measured by EPR spectroscopy and is discussed in terms of semi-empirical MO calculations.
A Facile Synthesis of Tetra- and Dihydronaphthalene Derivatives by Excimer Laser Photolysis of 1,2-Bis(substituted-methyl)benzenes in the Presence of Olefins and Acetylene
Ouchi, Akihiko,Koga, Yoshinori
, p. 7376 - 7383 (2007/10/03)
o-Quinodimethane (3A) was generated effectively by excimer laser photolyses of 1,2-bis(phenoxymethyl)benzene (1-O), 1,2-bis[(phenylthio)methyl]benzene (1-S), and 1,2-bis[(phenylseleno)methyl]-benzene (1-Se) in acetonitrile solutions via a two-photon process, which was followed by cycloaddition of 3A with several dienophlles-maleic anhydride (4a), dimethyl maleate (4b), dimethyl fumarate (4c), fumaronitrile (4d), and dimethyl acetylenedicarboxylate (4e) - to give corresponding cycloadducts 5. Three kinds of excimer lasers, namely, KrF (248 nm), XeCl (308 nm), and XeF (351 nm) excimer lasers were used for the reaction. The KrF excimer laser was found to be most effective for obtaining high consumption of 1-(O, S, Se) and yield of 5; the maximum yield of the cycloadduct obtained was 48%.
2,3-DICARBOMETHOXY-1,3-BUTADIENE AND ITS REACTIONS
Tarnchompoo, Bongkoch,Thebtaranonth, Chachanat,Thebtaranonth, Yodhathai
, p. 6671 - 6674 (2007/10/02)
The preparation of 2,3-dicarbomethoxy-1,3-butadiene from flash vacuum pyrolysis of 3 (itself obtained from methylenation of 2) is described.The diene's reactions with nucleophiles and dienophiles are also reported.
A New Route to 4-Hydroxytetralones and 1-Naphthols
Broom, Nigel J. P.,Sammes, Peter G.
, p. 465 - 470 (2007/10/02)
The lithium salts, derived from position 3 of phthalides by treatment with hindered bases, participate in Michael addition reactions with a variety of conjugated olefins.For singly activated olefins the conjugate anion reacts intramolecularly with the lactone group to produce 4-hydroxytetralones in moderate to good yield.Dehydration of these hydroxytetralones, by brief treatment with acid, produces the corresponding α-naphthol.Substituted phthalides react similarly making the method a general one for the production of substituted α-naphthols.
