19384-00-0Relevant articles and documents
Direct introduction of a boryl substituent into the 2-position of azulene: Application of the Miyaura and Smith methods to azulene
Kurotobi, Kei,Miyauchi, Masato,Takakura, Katsuto,Murafuji, Toshihiro,Sugihara, Yoshikazu
, p. 3663 - 3665 (2003)
The 4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl group was directly introduced into the 2-positions of azulenes with high selectivity by the C-H activation method with use of iridium catalysis. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
[2 + 2] Cycloaddition reaction of cycloheptatriene with dichloroketene. A novel and efficient synthetic strategy for the synthesis of 2-hydroxyazulene
Yokoyama,Ito,Watanabe,Harada,Kabuto,Morita
, p. 2257 - 2261 (2001)
The reaction of cycloheptatriene with dichloroketene, generated by the treatment of trichloroacetyl chloride with activated zinc in dry diethyl ether, affords 9,9-dichlorobicyclo[5.2.0]nona-2,4-dien-8-one 2 as a major product together with 3′,3′,9,9-tetrachlorospiro(bicyclo[5.2.0]nona-2,4-diene-8, 2′-oxetan)-4′-one 3. Structure 3 is elucidated by the X-ray crystallographic analysis of its partially reduced product. Lactone 3 exhibits [1,5] hydrogen-migration in the seven-membered ring to give 3′,3′,9,9-tetrachlorospiro(bicyclo[5.2.0]nona-3,5-diene-8, 2′-oxetan)-4′-one 7 without any decarbonylation. The reaction of 2 with diazomethane exhibits ring expansion of the four-membered ring to give 1,1-dichloro-3,3a,4,8a-tetrahydroazulen-2(1H)-one 8. 2-Hydroxyazulene 9 is successfully derived by the reaction of 8 with lithium chloride in good yield. The reaction of 8 with triethylamine exhibits dehydrochlorination to give 3-chloro-8,8a-dihydroazulen-2(1H)-one 10 in high yield. N-(Azulen-2-yl)pyrrolidine is also derived from either 9 or 10 in good yield.
Azulene methacrylate polymers: Synthesis, electronic properties, and solar cell fabrication
Puodziukynaite, Egle,Wang, Hsin-Wei,Lawrence, Jimmy,Wise, Adam J.,Russell, Thomas P.,Barnes, Michael D.,Emrick, Todd
, p. 11043 - 11049 (2014)
We report the synthesis of novel azulene-substituted methacrylate polymers by free radical polymerization, in which the azulene moieties represent hydrophobic dipoles strung pendant to the polymer backbone and impart unique electronic properties to the polymers. Tunable optoelectronic properties were realized by adjusting the azulene density, ranging from homopolymers (having one azulene group per repeat unit) to copolymers in which the azulene density was diluted with other pendant groups. Treating these polymers with organic acids revealed optical and excitonic behavior that depended critically on the azulene density along the polymer chain. Copolymers of azulene with zwitterionic methacrylates proved useful as cathode modification layers in bulk-heterojunction solar cells, where the relative azulene content affected the device metrics and the power conversion efficiency reached 7.9%.
Antiretroviral (HIV-1) activity of azulene derivatives
Peet, Julia,Selyutina, Anastasia,Bredihhin, Aleksei
, p. 1653 - 1657 (2016)
The antiretroviral activity of azulene derivatives was detected for the first time. A series of eighteen diversely substituted azulenes was synthesized and tested in vitro using HIV-1 based virus-like particles (VLPs) and infectious HIV-1 virus in U2OS and TZM-bl cell lines. Among the compounds tested, the 2-hydroxyazulenes demonstrated the most significant activity by inhibiting HIV-1 replication with IC50 of 2-10 and 8-20 μM for the VLPs and the infectious virus, respectively. These results indicate that azulene derivatives may be potentially useful candidates for the development of antiretroviral agents.
Syntheses and properties of linear π-conjugated molecules composed of 1-azaazulene and azulene
Ohtsu, Keito,Hayami, Ryohei,Sagawa, Takuya,Tsukada, Satoru,Yamamoto, Kazuki,Gunji, Takahiro
, (2019/10/14)
Two compounds, 6-(1-azaazulen-2-yl)ethynylazulene (8) and 6-(2-azulenyl)ethynylazulene (10), were synthesized using the Sonogashira-Hagihara cross-coupling reaction followed by decarboxylation with concentrated phosphoric acid. Compounds 8 and 10 were cha
Conformational analysis of N-aryl-N-(2-azulenyl)acetamides
Ito, Ai,Amaki, Takamasa,Ishii, Ayako,Fukuda, Kazuo,Yamasaki, Ryu,Okamoto, Iwao
supporting information, p. 3994 - 3998 (2018/10/02)
Aromatic amides bearing 2-azulenyl group on the amide nitrogen were synthesized and their structures were investigated. The π-electron density of the N-aryl group was found to influence the cis-trans conformational preferences of these compounds in solution. X-ray crystallography revealed that the plane of the 2-azulenyl ring has a strong tendency to lie coplanar with the amide plane when the azulene group is located on the same side as the amide oxygen atom.
Syntheses and Tunable Emission properties of 2-alkynyl azulenes
Koch, Michael,Blacque, Olivier,Venkatesan, Koushik
supporting information; experimental part, p. 1580 - 1583 (2012/06/05)
Various substituted 2-azulenes have been synthesized via Sonogashira coupling. Doping with superacids allows tunable emission from 443 to 750 nm depending on the substitution. The proton doped compounds are the first azulene alkyne based systems that show emission originating only from the S1 excited state.
An easy access to 2-substituted azulenes from azulene-2-boronic acid pinacol ester
Fujinaga, Masayuki,Suetake, Kouichi,Gyoji, Kazuhiro,Murafuji, Toshihiro,Kurotobi, Kei,Sugihara, Yoshikazu
scheme or table, p. 3745 - 3748 (2009/06/18)
Azulene-2-boronic acid pinacol ester was conveniently transformed into 2-substituted azulenes bearing carboxyl, formyl, ester, or amino groups, which are difficult to access by conventional methods. Furthermore, the azulene-2-carboxylic acid thus synthesized was subjected to the Ugi four-component condensation to obtain a dipeptide-type product containing an azulene skeleton. Georg Thieme Verlag Stuttgart.
Synthesis of 2-aminoazulene derivatives. Nucleophilic and palladium-catalyzed amination of 2-substituted azulene
Yokoyama, Ryuji,Ito, Shunji,Okujima, Tetsuo,Kubo, Takahiro,Yasunami, Masafumi,Tajiri, Akio,Morita, Noboru
, p. 8191 - 8198 (2007/10/03)
Amination of 2-substituted azulene was carefully examined using several types of amines, and the scope and limitation of substrates and reagents in these direct nucleophilic aminations were found. The synthesis of 2-aminoazulenes was successfully achieved by the reaction of 2-bromoazulene with several amines via palladium-catalyzed amination.
