3355-05-3Relevant academic research and scientific papers
Cascade reaction of 2,3-naphthalenediol with benzene in the presence of aluminum halides
Zhu, Zhongwei,Salnikov, George E.,Koltunov, Konstantin Yu.
, p. 857 - 859 (2019/02/24)
2,3-Naphthalenediol on superelectrophilic activation with aluminium halides smoothly reacts with benzene to give 4-((3-phenyl-1H-inden-1-yl)methyl)benzene-1,2-diol, which in turn undergoes intramolecular cyclization to form 5,10-methano-5-phenyldibenzo[a,d]cycloheptane-2,3-diol. The mechanistic aspects of these unusual transformations are discussed.
Regioselective and Chemoselective Reduction of Naphthols Using Hydrosilane in Methanol: Synthesis of the 5,6,7,8-Tetrahydronaphthol Core
He, Yuan,Tang, Jinghua,Luo, Meiming,Zeng, Xiaoming
supporting information, p. 4159 - 4163 (2018/07/29)
A regioselective and chemoselective method for catalytic synthesis of biologically interesting 5,6,7,8-tetrahydronaphthols by reduction of naphthols was described. The side aromatic hydrocarbons in naphthols were site-selectively reduced, using hydrosilanes in methanol, allowing for retaining functional phenol scaffolds intact. It presents a rare example of using low-cost and air-stable hydrosilane for catalytic reduction of unactivated aromatic hydrocarbons under mild conditions. This reaction is scalable and proceeds in high selectivity without the formation of 1,2,3,4-tetrahydronaphthol byproducts with toleration of sensitive functionalities such as bromide, chloride, fluoride, ketone, ester, and amide.
Development of an iron(II)-catalyzed aerobic catechol cleavage and biomimetic synthesis of betanidin
Guimond, Nicolas,Mayer, Peter,Trauner, Dirk
supporting information, p. 9519 - 9523 (2014/08/18)
An aerobic iron(II)-catalyzed cleavage of catechols was developed. This reaction allows for the preparation of 2-methoxy-2H-pyrans that can be employed as versatile building blocks for synthesis. The utility of this biomimetic oxidative cleavage is featured in the synthesis of betanidin, a natural colorant with antioxidant properties. Cut and paste: An aerobic iron(II)-catalyzed oxidative cleavage of catechol was developed. This reaction allows the preparation of 2H-pyrans that can be employed as versatile building blocks for synthesis. The utility of this biomimetic cleavage is featured in the synthesis of betanidin, the aglycone of red beets' principal colorant and itself a valuable antioxidant (see scheme).
Synthesis of catechols from phenols via Pd-catalyzed silanol-directed C-H oxygenation
Huang, Chunhui,Ghavtadze, Nugzar,Chattopadhyay, Buddhadeb,Gevorgyan, Vladimir
supporting information; experimental part, p. 17630 - 17633 (2011/12/16)
A silanol-directed, Pd-catalyzed C-H oxygenation of phenols into catechols is presented. This method is highly site selective and general, as it allows for oxygenation of not only electron-neutral but also electron-poor phenols. This method operates via a silanol-directed acetoxylation, followed by a subsequent acid-catalyzed cyclization reaction into a cyclic silicon-protected catechol. A routine desilylation of the silacyle with TBAF uncovers the catechol product.
A new entry to the synthesis of 1,2-benzenediol congeners
Ozaki,Oshio,Ohsuga,Kaburagi,Sung,Kim
, p. 1132 - 1136 (2007/10/02)
1,2-Benzenediols were synthesized via 1,1-bis(ethylthio)-3-cyclohexen-2-one derivatives, which were prepared by condensation of 1,1-bis(ethylthio)-2-propanone with Mannich bases. Regioselective preparation of their monoethers was also achieved.
A NEW ENTRY TO 1,2-BENZENEDIOL CONGENERS
Ozaki, Yutaka,Oshio, Ikumi,Kim, Sang-Won
, p. 1434 - 1436 (2007/10/02)
1,2-Benzenediols and their monoethers were efficiently prepared from α,α-bis(ethylthio)cyclohexenones which were constructed by the C3+C3 annulation of 1,1-bis(ethylthio)propan-2-one and the Mannich bases. KEYWORDS 1,2-benzenediol; aromatic synthesis; annulation; aromatic compound; acetal
Substituted 1,2,3,4-Tetrahydroaminonaphthols: Antihypertensive Agents, Calcium Channel Blockers, and Adrenergic Receptor Blockers with Catecholamine-Depleting Effects
Atwal, Karnail S.,O'Reilly, Brian C.,Ruby, Eric P.,Turk, Chester F.,Aberg, Gunnar,et al.
, p. 627 - 635 (2007/10/02)
Substituted 1,2,3,4-tetrahydroaminonaphthols were found to be calcium channel blockers with antihypertensive properties.These compounds also possessed adrenergic β-receptor blocking activity.From the structure-activity studies, no clear correlation emerged between the in vitro calcium channel blocking activity and the acute antihypertensive activity in cannulated spontaneously hypertensive rats.Extensive pharmacological testing of selected compounds indicated that aminonaphthols are antihypertensive agents with many pharmacological properties.The relative contribution of various pharmacological actions toward the observed antihypertensive activity is unclear.Since the clinically useful calcium channel blocker verapamil is structurally related to these compounds, one of the aminonaphthols, trans-3--1,2,3,4-tetrahydro-6,7-dimethoxy-2-naphthalenol (12), was compared with verapamil for calcium channel blocking activity, adrenergic blocking activity, and catecholamine-depleting activity.Both compopunds were found to be equipotent in these test systems.
