57189-64-7Relevant academic research and scientific papers
Metal triflate promoted synthesis of naphthalenes
Chan, Chieh-Kai,Wang, Heui-Sin,Tsai, Yu-Lin,Chang, Meng-Yang
, p. 29321 - 29329 (2017)
A synthetic route to derive the skeleton of naphthalenes starting with isovanillin is described with modest total yields via the key transformation of metal triflate-mediated intramolecular benzannulation of o-formyl or o-benzoyl allylbenzenes in MeNO2 at rt.
Fused Catechol Ethers from Gold(I)-Catalyzed Intramolecular Reaction of Propargyl Ethers with Acetals
Pati, Kamalkishore,Dos Passos Gomes, Gabriel,Harris, Trevor,Alabugin, Igor V.
supporting information, p. 928 - 931 (2016/03/15)
Selective gold(I)-catalyzed rearrangement of aromatic methoxypropynyl acetals leads to fused catechol ethers (1,2-dialkoxynapthalenes) in excellent yields. Furthermore, this process extends to the analogous heterocyclic and aliphatic substrates. Alkyne activation triggers nucleophilic addition of the acetal oxygen that leads to an equilibrating mixture of oxonium ions of similar stability. This mixture is "kinetically self-sorted" via a highly exothermic cyclization. Selective formation of 1,2-dialkoxy naphthalenes originates from chemoselective aromatization of the cyclic intermediate via 1,4-elimination of methanol.
Syntheses of substituted naphthalenes and naphthols
Huang, Keng-Shiang,Wang, Eng-Chi,Chen, Hsing-Ming
, p. 585 - 605 (2007/10/03)
Syntheses of substituted naphthalenes and naphthols are described. Based on Claisen rearrangement, ring-closing metathesis (RCM), and related reactions, isovanillin was successfully transformed into a series of substituted naphthalenes and naphthols with
N-(2-phenyl-4-piperidinybutyl)-5,6,7,8-tetrahydro-1-naphthalenecarboxamides and their use as neurokinin 1 (NK1) and/or neurokinin 2 (NK2) receptor antagonists
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, (2008/06/13)
Compounds of formula (I), wherein R2is a 5,6,7,8-tetrahydronaphth-1-yl group which may be substituted (the remaining groups defined herein), and pharmaceutical compositions containing the compounds and methods of using the compounds in the treatment of a condition where antagonism of the NK1 and/or NK2 receptors is beneficial.
A novel synthesis of substituted naphthalenes via Claisen rearrangement and RCM reaction
Huang, Keng-Shiang,Wang, Eng-Chi
, p. 6155 - 6157 (2007/10/03)
A novel synthesis of substituted naphthalenes was studied. Starting from isovanillin, basing on Claisen rearrangement and ring-closing metathesis (RCM), a series of 1-alkoxy-2-methoxynaphthalenes and 1-alkoxy-2-methoxy-8-methylnaphthalenes together with a
LANTHANIDE-INDUCED SHIFTS OF STERICALLY HINDERED AROMATIC o-DIMETHOXY COMPOUNDS: MODEL COMPOUNDS AND o-DIMETHOXYCOUMARINS
Hofer, Otmar
, p. 715 - 720 (2007/10/02)
The lanthanide-induced shifts (LIS) of a series of sterically hindered o-dimethoxy compounds, characterized by a 3-substituted 1,2-dimethoxy unit as a structural element, were simulated in model calculations.Development of a generally suitable computational model for aromatic o-dimethoxycompounds allows prediction of relative LIS values for o-dimethoxy complexation.The model was used for several naturally occurring dimethoxycoumarins taking into account the population ratios of the two possible co-ordinating sites in these molecules (o-dimethoxy and lactone carbonyl).
Product and mechanistic studies of the anodic oxidation of methoxylated naphthalenes. The EECrCp mechanism
Dolson, Mark G.,Swenton, John S.
, p. 2361 - 2371 (2007/10/21)
The anodic oxidations of 1- and 2-methoxy- and 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 2,3-, 2,6-, and 2,7-dimethoxynaphthalenes have been studied in methanolic potassium hydroxide. At lower temperatures (0-20°C) the major process in 1-methoxynaphthalene and 1,5-, 1,6-, and 1,7-dimethoxynaphthalenes is two-electron oxidation resulting in addition of methoxy groups across the 1,4-positions followed by loss of methanol on workup to afford the methoxylated naphthalene. In contrast, 2-methoxynaphthalene and 1,3-, 2,3-, 2,6-, and 2,7-dimethoxynaphthalenes give major amounts of products derived from four-electron oxidation under these conditions. When the anodic oxidation of this first class of compounds was conducted in refluxing methanol, increased amounts of four-electron oxidation products were isolated. While 1-methylnaphthalene and naphthalene also undergo anodic oxidation under these conditions, these unactivated systems react less selectively and efficiently. Mechanistic studies are most consistent with the key step of the anodic oxidation under these conditions being the reaction of methoxy radical with the aromatic radical cation. This reaction sequence is termed the EECrCp mechanism, and the results of the oxidation of the methoxylated naphthalenes above are discussed in this format.
