42877-08-7Relevant academic research and scientific papers
2-Ethynyl-6-methylthieno[3,2-b]thiophene as an efficient π spacer for porphyrin-based dyes
Zhao, Huifang,Long, Jun,Luo, Xi,Zhao, Bin,Tan, Songting
, p. 168 - 176 (2015)
In this study, three donor-π-acceptor (D-π-A) type unsymmetrical porphyrin-based dyes have been designed and synthesized for dye-sensitized solar cells (DSSCs). The photophysical, electrochemical and photovoltaic properties of the dyes were successfully a
Metathesis reactions for the synthesis of ring-fused carbazoles
Pelly, Stephen C.,Parkinson, Christopher J.,Van Otterlo, Willem A. L.,De Koning, Charles B.
, p. 10474 - 10481 (2005)
The metathesis reaction is used as a key step for the synthesis of the indolo[2,3-α]carbazole core of rebeccamycin 13 and the sulfur analog of furostifoline 21. Using the same methodology for the attempted synthesis of furostifoline, we unexpectedly formed tert-butyl-2a-methyl-1,2,2a,10c- tetrahydro-6H-cyclobuta[c]furo[3,2-α]carbazole-6-carboxylate 26 from the unstable diene, tert-butyl 2-(2-isopropenyl-3-furyl)-3-vinyl-1H-indole-1- carboxylate 25, presumably via a spontaneous π8 electrocyclization reaction.
α-Oxocarboxylic Acids as Three-Carbon Insertion Units for Palladium-Catalyzed Decarboxylative Cascade Synthesis of Diverse Fused Heteropolycycles
Zhou, Liwei,Qiao, Shujia,Zhou, Fengru,Xuchen, Xinyu,Deng, Guobo,Yang, Yuan,Liang, Yun
supporting information, p. 2878 - 2883 (2021/05/05)
A novel palladium-catalyzed decarboxylative cascade cyclization for the assembly of diverse fused heteropolycycles by employing α-oxocarboxylic acids as three-carbon insertion units is reported. This protocol enables the synthesis of isoquinolinedione- and indolo[2,1-a]isoquinolinone-fused benzocycloheptanones in moderate to good yields by the use of different aryl iodides, including alkene-tethered 2-iodobenzamides and 2-(2-iodophenyl)-1H-indoles. Notably, the approach achieves simultaneous construction of both six- and seven-membered rings via sequential intramolecular carbopalladation, C-H activation, and decarboxylation.
"one-Pot" Synthesis of γ-Pyrones from Aromatic Ketones/Heteroarenes and Carboxylic Acids
Sun, Xiangyu,Gong, Ming,Huang, Mengmeng,Li, Yabo,Kim, Jung Keun,Kovalev, Vladimir,Shokova, Elvira,Wu, Yangjie
, p. 15051 - 15061 (2020/12/02)
Despite the various attractive properties of γ-pyrones, there are still some deficiencies in their synthetic approaches such as lower atom economy, multistep processes, and prefunctionalization of the reagents. In this work, an efficient and simple (CF3CO
Formation of substituted 1-naphthols and related products via dimerization of alkyl 3-(o-halo(het)aryl)-oxopropanoates based on a CuI-catalyzed domino C-arylation/condensation/aromatization process
Weischedel, Heike,Sudheendran, Kavitha,Mikhael, Alevtina,Conrad, Jürgen,Frey, Wolfgang,Beifuss, Uwe
, p. 3454 - 3467 (2016/06/06)
Substrates bearing both a β-ketoester moiety and a (het)aryl halide structure element were dimerized to 1-naphthols and related products in the presence of catalytic amounts of CuI in isopropanol. The reaction starts with an intermolecular C-arylation, which is followed by an intramolecular condensation. The final aromatization delivers the highly substituted products with yields up to 81%.
Molecular structure-intersystem crossing relationship of heavy-atom-free bodipy triplet photosensitizers
Ji, Shaomin,Ge, Jie,Escudero, Daniel,Wang, Zhijia,Zhao, Jianzhang,Jacquemin, Denis
, p. 5958 - 5963 (2015/06/16)
A thiophene-fused BODIPY chromophore displays a large triplet-state quantum yield (φT = 63.7%). In contrast, when the two thienyl moieties are not fused into the BODIPY core, intersystem crossing (ISC) becomes inefficient and φT remains low (φT = 6.1%). First-principles calculations including spin-orbit coupling (SOC) were performed to quantify the ISC. We found larger SOC and smaller singlet-triplet energy gaps for the thiophene-fused BODIPY derivative. Our results are useful for studies of the photochemistry of organic chromophores.
Direction of 3-bromothiophene acylation with succinyl chloride
Smirnov,Afanas'Ev,Prostakishin,Belen'Kii
, p. 386 - 391 (2013/07/26)
In the reaction of 3-bromothiophene with succinyl chloride in the presence of AlCl3, a mixture of three isomeric dibromo-substituted 1,4-di(2-thienyl)butane-1,4-diones was formed. The main component was the unsymmetrical 1-(3-bromo-2-thienyl)-4-(4-bromo-2-thienyl)butane-1,4-dione rather than 1,4-di-(3-bromo-2-thienyl)butane-1,4-dione expected according to the orientation rules.
Synthesis and characterization of some novel 3-bromo-2-acetylthiophene chalcones and biological evaluation of their ethyl-4-(3-bromothien-2-yl)-2-oxo- 6-(aryl)cyclohex-3-ene-1-carboxylate derivatives
Ashalatha,Narayana,Vijaya Raj
experimental part, p. 1904 - 1919 (2010/02/28)
Novel chalcones 1-(3-bromothien-2-yl)-3-(aryl)prop-2-en-1-ones derived from 3-bromo-2-acetylthiophene and their cyclization product with ethylacetoacetate such as 4-(3-bromothien-2-yl)-2-oxo-6-(aryl)cyclohex-3-ene-1-carboxylate derivatives were synthesize
Synthesis of 2,3-Substituted Thienylboronic Acids and Esters
Christophersen, Claus,Begtrup, Mikael,Ebdrup, Soren,Petersen, Henning,Vedso, Per
, p. 9513 - 9516 (2007/10/03)
A noncryogenic protocol for the synthesis of 2-substituted 3-thienylboronic acids and esters as well as 3-substituted 2-thienylboronic acids and esters has been developed. Electrophiles were introduced regiospecifically in the 2-position of 2,3-dibromothiophene and in the 3-position of 2-bromo-3-iodothiophene by halogen-magnesium exchange followed by quenching with electrophiles. Palladium-catalyzed borylation of the 2,3-substituted halothiophenes with pinacolborane and P(t-Bu)3 as ligand for Pd produced 9 and 10. The borylation protocol was tolerated by a range of functional groups; however, strongly electron-withdrawing substituents decreased the stability of the thienylboronic acids and esters.
Preparation of benzene, furan, and thiophene analogs of duocarmycin SA employing a newly-devised phenol-forming reaction
Muratake,Hayakawa,Natsume
, p. 1558 - 1566 (2007/10/03)
Five A-ring analogs of duocarmycin SA 9a - e were synthesized in racemic form modifying our second synthetic route toward duocarmycin SA. The problem encountered at the crucial phenol forming step to secure 17a, b from 16a, b under the conventionally used
