613-06-9Relevant articles and documents
Synthesis of annulated arenes and heteroarenes by hydriodic acid and red phosphorus mediated reductive cyclization of 2-(Hetero)aroylbenzoic acids or 3-(Hetero)arylphthalides
Rafiq, Settu Muhamad,Mohanakrishnan, Arasambattu K.
supporting information, p. 362 - 370 (2017/02/10)
Annulated arenes and hetarenes were prepared in good to very good yields by hydriodic acid/red phosphorus mediated reductive cyclization of 3-(hetero)aryl phthalides. The reductive cyclization also proceeded successfully with 2-aroylbenzoic acids and 2-aroylnaphthoic acids.
Synthesis of Annulated Anthracenes, Carbazoles, and Thiophenes Involving Bradsher-Type Cyclodehydration or Cyclization-Reductive-Dehydration Reactions
Rafiq, Settu Muhamad,Sivasakthikumaran, Ramakrishnan,Karunakaran, Jayachandran,Mohanakrishnan, Arasambattu K.
, p. 5099 - 5114 (2015/08/18)
A conventional BF3·OEt2-mediated Bradsher-type cyclodehydration of 2-arylmethyl benzaldehydes in CH2Cl2 at room temperature gave polycyclic aromatic and heteroaromatic compounds. Alternatively, these compounds could be synthesized in better yields from 2-arylmethylbenzoic acids by triflic-acid-mediated cyclization followed by reductive dehydration.
Synthesis of tetrafunctionalized pentiptycenequinones for construction of cyclic dimers with a cylindrical shape by boronate ester formation
Akine, Shigehisa,Kusama, Daisuke,Takatsuki, Yuri,Nabeshima, Tatsuya
, p. 4880 - 4884 (2015/07/28)
Abstract New tetrasubstituted pentiptycenequinone derivatives 1 and 2 having two sets of diol moieties in a syn orientation were synthesized from the corresponding 2,3-disubstituted anthracene derivatives. The semicircular scaffold of these molecules is expected to be useful to create a belt-like structure having an aromatic π-wall. Indeed, the reaction of 1 with 1,4-phenylenediboronic acid or 4,4′-biphenyldiboronic acid quantitatively gave a 2:2 macrocyclic product via boronate ester formation. The efficient formation of these cyclic structures can be explained by favorable intramolecular cyclization at the final step.
A versatile synthesis of annulated carbazole analogs involving a domino reaction of bromomethylindoles with arenes/heteroarenes
Dhayalan, Vasudevan,Clement, J. Arul,Jagan, Radhakrishnan,Mohanakrishnan, Arasambattu K.
experimental part, p. 531 - 546 (2009/09/06)
A ZnBr2-mediated arylation of aryl/heteroaryl methyl bromides with arenes at 80°C led to the formation of arylated products, which underwent subsequent 1,5-sigmatropic rearrangement followed by electrocyclization and aromatiza tion with loss of a diethylmalonate unit to afford the corresponding annulated products.
Nitrous oxide oxidation catalyzed by ruthenium porphyrin complex
Tanaka, Hirotaka,Hashimoto, Kentaro,Suzuki, Kyosuke,Kitaichi, Yasunori,Sato, Mitsuo,Ikeno, Taketo,Yamada, Tohru
, p. 1905 - 1914 (2007/10/03)
Dinitrogen oxide was employed as a clean oxidant for various oxidations in the presence of a catalytic amount of dioxoruthenium tetramesitylporphyrin complex (Ru(tmp)(O)2). A variety of olefins, secondary alcohols, and benzyl alcohols were smoothly oxidized to the corresponding epoxides, ketones, and aldehydes in high yields. In the oxidation of 9,10-dihydroanthracene derivatives, the competitive reactions affording anthraquinones and anthracenes could be regulated by the reaction conditions. At a high temperature (200°C), anthraquinones were selectively produced, while the anthracenes were selectively produced by the addition of sulfuric acid.
Efficient oxidative aromatization of 9,10-dihydroanthracenes with molecular oxygen catalyzed by ruthenium porphyrin complex
Tanaka, Hirotaka,Ikeno, Taketo,Yamada, Tohru
, p. 576 - 578 (2007/10/03)
In the presence of a catalytic amount of a ruthenium porphyrin complex, various 9,10-dihydroanthracene derivatives were aromatized with molecular oxygen to the corresponding anthracenes. It was found that the addition of sulfuric acid accelerated the aromatization at room temperature under atmospheric pressure of oxygen to afford various anthracenes in high yields.
Selective nitrous oxide oxidation for C-H oxidation and aromatization of 9,10-dihydroanthracene derivatives
Hashimoto, Kentaro,Tanaka, Hirotaka,Ikeno, Taketo,Yamada, Tohru
, p. 582 - 583 (2007/10/03)
During the nitrous oxide oxidation of 9,10-dihydroanthracene derivatives catalyzed by the ruthenium-porphyrin complexes, anthraquinones were selectively afforded by the C-H oxidation of the benzylic carbon under the appropriate reaction conditions, whereas anthracenes as a result of oxidative aromatization were selectively obtained in the presence of sulfuric acid.
An Efficient Reduction of Anthrones to Anthracenes
Marquardt, Donald J.,McCormick, Frankie A.
, p. 1131 - 1134 (2007/10/02)
An efficient and general means of reducing anthrones to anthracenes has been developed.The procedure, which uses NaBH4 as the reducing agent in a mixed solvent system of diglyme/methanol, produced anthracenes in essentially quantitative yield from a variety of anthrones.
