55700-10-2Relevant academic research and scientific papers
Direct Oxidative Arylation of C(sp3)-H Bonds Adjacent to Oxygen of Ethers and Alcohols
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Paragraph 0022; 0079; 0095; 0096, (2017/04/26)
The present invention relates to a method for arylating ethers or alcohols through a C(sp^3)-H bond activity. More specifically, according to the method of the present invention, phenol which does not have a functional group such as -B(OH)_2 in ethers or alcohols reacts under a transition metal catalyst, so a novel-type sp^3C-H bond can be synthesized. The method does not have separately introduce a -B(OH)_2 functional group to a benzene ring. Phenol derivatives or naphthalene derivatives which can be commercially purchased react, so ethers or alcohols can be directly connected with a benzene ring including an OH group.COPYRIGHT KIPO 2017
Synthesis and anticancer properties of new (dihydro)pyranonaphthoquinones and their epoxy analogs
Dang Thi, Tuyet Anh,Vu Thi, Thu Ha,Thi Phuong, Hoang,Ha Nguyen, Thanh,Pham The, Chinh,Vu Duc, Cuong,Depetter, Yves,Van Nguyen, Tuyen,D'Hooghe, Matthias
, p. 3355 - 3358 (2015/07/08)
Abstract 1,4-Dihydroxy-2-naphthoic acid was used as a substrate for a straightforward five-step synthesis of 3-substituted 1H-benzo[g]isochromene-5,10-diones, with a Michael addition of N-acylmethylpyridinium ylides across 2-hydroxymethyl-1,4-naphthoquino
Synthesis of 2-[(4-[18F]Fluorobenzoyloxy)methyl]-1,4- naphthalenedione from 2-hydroxymethyl 1,4-naphthoquinone and 4-[ 18F]fluorobenzoic acid using dicyclohexyl carbodiimide
Ackermann, Uwe,Sigmund, Duanne,Yeoh, Shinn Dee,Rigopoulos, Angela,O'Keefe, Graeme,Cartwright, Glenn,White, Jonathan,Scott, Andrew M.,Tochon-Danguy, Henri J.
scheme or table, p. 788 - 794 (2012/05/20)
2-[(4-[18F]Fluorobenzoyloxy)methyl]-1,4-naphthalenedione ([ 18F]1) was synthesised as a putative hypoxia imaging agent from 2-hydroxymethyl 1,4-naphthoquinone (7) and 4-[18F]fluorobenzoic acid ([18F]8) using dicyclohexyl carbodiimide (DCC) to activate [ 18F]8. This coupling reaction was fast and gave quantitative yields. Further investigations are warranted on the use of DCC as a coupling agent in Positron Emission Tomography. The synthesis including HPLC purification and reformulation has been fully automated on a modified FDG synthesiser with two reactor vials. [18F]1 was produced in a radiochemical yield of 27 ± 5%, with a radiochemical purity of 97.5% and a specific activity of 78.4-134.5 GBq/μmol at the end of synthesis (n = 23). The total synthesis time including reformulation was 65 min. [18F]1 was found to be stable in plasma and saline, but underwent rapid metabolism in a phase 1 metabolite assay using rat S9 liver fractions. An in vivo evaluation of [ 18F]1 in transplanted, hypoxic SK-RC-52 tumour-bearing BALB/c nude mice revealed the tumour-to-muscle ratio to be 2.4 ± 0.1 at 2 h post-injection.
An efficient method for the one-pot construction of the 1H-naphtho[2,3-c]pyran-5,10-dione system
Kobayashi, Kazuhiro,Uchida, Masaharu,Uneda, Tomokazu,Yoneda, Keiichi,Tanmatsu, Miyuki,Morikawa, Osamu,Konishi, Hisatoshi
, p. 2977 - 2982 (2007/10/03)
2-(1-Hydroxyalkyl)-1,4-naphthoquinones are found to react with pyrrolidino enamines in toluene to give 1H-naphtho[2,3-c]pyran-5,10-diones in good yields via a tandem conjugate addition-cyclization sequence, followed by an elimination of pyrrolidine. 2-Hydroxymethyl-1,4-naphthoquinone and morpholino enamines undergo a similar sequence, without loss of morpholine, to yield 3-morpholino-3,4-dihydro-1H-naphtho[2,3-c]pyran-5,10-diones. The 3-morpholino group of these products can be replaced with a hydro, a hydroxy, or a methoxy group. Imines also react with 2-(1-hydroxyalkyl)-1,4-naphthoquinones to give the corresponding 1H-naphtho[2,3-c]pyran-5,10-diones, including a natural product (pentalongin). The utility of these reactions is demonstrated in the synthesis of pyranonaphthoquinone antibiotics, viz. (±)-eleutherin and (±)-isoeleutherin.
Synthesis of quinones from hydroquinone dimethyl ethers. Oxidative demethylation with cobalt(III) fluoride
Tomatsu, Ayumi,Takemura, Syunji,Hashimoto, Kimiko,Nakata, Masaya
, p. 1474 - 1476 (2007/10/03)
The oxidative demethylation of 1,4-dimethoxynaphthalene and 1,4- dimethoxybenzene derivatives with cobalt(III) fluoride proceeded in good to excellent yield to afford the corresponding naphthoquinone and benzoquinone derivatives.
Microwave-induced Monohydroxymethylation and Monoalkoxylation of 1,4-Naphthoquinones
Bansal, Vandana,Sharma, Jyotsana,Khanna, Rajinder N.
, p. 720 - 721 (2007/10/03)
1,4-Naphthoquinones and its derivatives have been hydroxymethylated and alkoxylated in the quinone ring using, respectively, formalin or an alcohol, in the presence of K2CO3 or HgO by heating or microwave irradiation.
Selective hydroxymethylation of naphthoquinones
Thapliyal, P. C.,Sharma, J.,Singh, K. P.,Khanna, R. N.
, p. 994 - 996 (2007/10/03)
Naphthoquinone and substituted naphthoquinones undergo selective hydroxymethylation at the quinonoid position with formalin in the presence of (a) sodium nitrite and iodine; (b) copper bronze; and (c) neutral alumina.
2-and 6-methyl-1,4-naphthoquinone derivatives as potential bioreductive alkylating agents
Antonini,Lin,Cosby,Dai,Sartorelli
, p. 730 - 735 (2007/10/02)
A number of antineoplastic agents possess both the quinone nucleus and an appropriate substituent that permits them to function as bioreductive alkylating agents. To develop new compounds of this type with unique properties, the authors have synthesized a
