110973-39-2Relevant academic research and scientific papers
Facile synthesis of benzoindoles and naphthofurans through carbonaceous material-catalyzed cyclization of naphthylamines/naphthols with nitroolefins in water
Zhang, Furen,Li, Chunmei,Wang, Chen,Qi, Chenze
, p. 5022 - 5029 (2015)
A facile and efficient approach has been established for the synthesis of benzoindole and naphthofuran derivatives via the metal-free cyclization reaction of nitroolefins with naphthylamines/naphthols. Various substituted benzoindoles and naphthofurans are obtained in good to excellent yields. Moreover, the ability to recycle the carbonaceous material makes this method quite cost-effective and environmentally benign compared to traditional acid-catalyzed methods. Theoretical studies indicated that the reaction between naphthylamine and nitroolefin catalyzed by this solid acid was thermodynamically controlled at 60 °C, resulting in the formation of the benzoindoles.
An Approach to the Synthesis of 1-Propenylnaphthols and 3-Arylnaphtho[2,1-b]furans
Huang, Jin,Wang, Wei,He, Hai-Yu,Jian, Lei,Fu, Hai-Yan,Zheng, Xue-Li,Chen, Hua,Li, Rui-Xiang
supporting information, p. 2523 - 2534 (2017/03/14)
A simple and efficient strategy for the synthesis of 1-propenylnaphthols from readily accessible 3-arylallylnaphthyl ethers has been developed. By using K2CO3 as base and 2-methoxyethanol as solvent, direct access to a wide range of
: NBu4NPF6 promoted regioselective cascade synthesis of functionally embellished naphthofurans under acid, metal & solvent free conditions
Pareek, Abhishek,Dada, Ravikrishna,Rana, Monika,Sharma, Anuj K.,Yaragorla, Srinivasarao
, p. 89732 - 89743 (2016/10/03)
nBu4NPF6 mediated highly regioselective synthesis of functionally embellished naphthofurans has been achieved from easily available naphthols and propargyl alcohols through a cascade benzylation, oxacyclisation (5-exo dig) and isomerization under solvent free conditions. The reaction works in a short time through dibenzyl ether formation followed by the decomposition to the carbocation to furnish the high yielding products with large substrate scope. The synthetic utility of the products is demonstrated through C(sp3)-H functionalization. In addition, we investigated selected naphthofurans for their anti-amyloidogenic properties. Preliminary studies suggest that these are excellent inhibitors for amyloid formation, a hallmark for several neurodegenerative diseases.
Br?nsted Acid Catalyzed Functionalization of Aromatic Alcohols through Nucleophilic Substitution of Hydroxyl Group
Mishra, Abhishek Kumar,Biswas, Srijit
, p. 2355 - 2363 (2016/04/04)
The hydroxyl groups of naphthol and tautomerizable phenol derivatives have been substituted by O-, S-, N-, and C-centered nucleophiles under solvent-free reaction conditions. The products are generated in good to excellent yields. para-Toluenesulfonic acid exhibits the best catalytic activity compared to other Bronsted acids. Experimental observations suggest that the reaction proceeds through the intermediacy of the keto tautomer of naphthol. Nucleophilic addition to the carbonyl group followed by elimination of water generates the desired product. The present methodology provides access to substituted naphtho[2,1-b]furan derivatives. The products generated using N-centered nucleophiles can be further transformed to important classes of organic molecules such as benzocarbazole and imidazole derivatives.
Diversified Synthesis of Furans by Coupling between Enols/1,3-Dicarbonyl Compounds and Nitroolefins: Direct Access to Dioxa[5]helicenes
Ghosh, Monoranjan,Santra, Sougata,Mondal, Pallab,Kundu, Dhiman,Hajra, Alakananda
, p. 2525 - 2536 (2015/10/29)
A versatile method for the diversified synthesis of furans and arenofurans has been developed that proceeds through K2CO3-promoted cyclization between enols/1,3-dicarbonyl compounds and nitroolefins at reflux in EtOH. This facile method has been successfully employed in the synthesis of benzotrifuran derivatives, which are useful hole-transporting materials. This procedure also provides direct access to dioxa[5]helicenes. This reaction offers a broad substrate scope, uses an inexpensive base and environmentally benign solvent, and is operationally simple.
A Simple and Efficient Access to Naphtho[b]furans by Claisen Rearrangement/Cyclization of Bromonaphthyl 3-Phenylallyl Ethers
Wang, Wei,Huang, Jin,Zhou, Rong,Jiang, Zhi-Jie,Fu, Hai-Yan,Zheng, Xue-Li,Chen, Hua,Li, Rui-Xiang
, p. 2442 - 2446 (2015/08/18)
A transition-metal-free Claisen rearrangement/cyclization reaction was developed for the synthesis of naphthofuran derivatives from bromonaphthyl 3-phenylallyl ethers. The nature of the base employed in this reaction plays an important role in determining the ratio for the formation of naphthofuran and naphthol products. By using K2CO3 as base and DMF as solvent, we have synthesized a variety of functionalized naphthofurans in good to high yields (49-92 %) and with satisfactory selectivities.
Iron-catalyzed direct synthesis of densely Substituted benzofurans and naphthopyrans from phenolic compounds and propargylic alcohols
Yuan, Feng-Quan,Han, Fu-She
supporting information, p. 537 - 547 (2013/05/08)
A one-pot cascade reaction for the synthesis of polysubstituted benzofurans and naphthopyrans from simple phenols and propargylic alcohols catalyzed by iron(III) is presented. The results demonstrate that the structural specificity for the formation of fu
Microwave-assisted Claisen rearrangement of naphthyl 2-propynyl ethers: Synthesis of naphthofurans
Prasada Rao Lingam,Dahale, Dnyaneshwar H.,Mukkanti, Kagga,Gopalan, Balasubramanian,Thomas, Abraham
, p. 5695 - 5698 (2012/10/29)
An efficient two-step approach for the synthesis of naphtho[1,2-b]furans and naphtho[2,1-b]furans has been developed. Various functionalized propargyl alcohols were etherified with α- or β-naphthol under Mitsunobu reaction conditions to give naphthyl 2-pr
Indium triflate-catalyzed coupling between nitroalkenes and phenol/naphthols: A simple and direct synthesis of arenofurans by a cyclization reaction
Kundu, Dhiman,Samim, Md,Majee, Adinath,Hajra, Alakananda
supporting information; experimental part, p. 406 - 409 (2011/10/12)
An eye furan eye: A simple and efficient protocol for the synthesis of benzofuran and naphthofuran derivatives catalyzed by indium triflate was developed by coupling α,β-unsaturated nitroalkenes with phenol/naphthols. The present method provides arenofuran derivatives in one pot from readily available starting materials (DCE=1,2-dichloroethane; see scheme). Copyright
