22913-25-3Relevant academic research and scientific papers
Diels-Alder reactions for the rational design of benzo[b]thiophenes: DFT-based guidelines for synthetic chemists
Brasca, Romina,Kneeteman, María N.,Mancini, Pedro M.E.,Fabian, Walter M.F.
, p. 158 - 168 (2012)
In this work we studied the capability of several diene/dienophile pairs to undergo Diels-Alder (DA) reactions leading to benzo[b]thiophenes. A variety of synthetically and commercially available nitrothiophenes were chosen as dienophiles. Methyl 5-nitro-3-thiophenecarboxylate was selected as a potential strong electrophilic candidate based on some DFT-based properties and the substitution pattern of the expected product. The mechanistic details concerning the participation of this dienophile in polar DA reactions were investigated through a theoretical point of view. The results were compared with the experimental outcomes. This methodology should allow synthetic chemists to analyze DA reactions in detail in a stage prior to the synthetic job.
METHOD FOR PROMOTING PLANT GROWTH
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Paragraph 0222; 0223, (2015/11/11)
The present invention provides a method for promoting plant growth, which comprises treating a plant with a compound represented by the following Formula (1): provided that a method for promoting plant growth which comprises treating plants with a compoun
Transition-metal-free transformation of aryl bromides into aromatic esters and amides via aryl trichloromethyl ketones
Dohi, Souya,Moriyama, Katsuhiko,Togo, Hideo
, p. 7815 - 7822 (2013/12/04)
A variety of aryl bromides have been treated with Mg and then chloral, followed by tBuOCl and subsequently alcohols or amines to produce the corresponding aromatic esters or amides in good yields via the formation of aryl trichloromethyl ketones as intermediates. These reactions are examples of a transition-metal-free one-pot preparation of aromatic esters and amides from aryl bromides. Aryl bromides have been treated with Mg and then chloral, followed by tBuOCl or tBuOCl with I2 as an additive, and subsequently alcohols or amines to form the corresponding aromatic esters and aromatic amides via aryl trichloromethyl ketones as intermediates. Copyright
Direct benzothiophene formation via oxygen-triggered intermolecular cyclization of thiophenols and alkynes assisted by manganese/PhCOOH
Liu, Kaisheng,Jia, Fan,Xi, Hui,Li, Yuanming,Zheng, Xiaojian,Guo, Qiaoxia,Shen, Baojian,Li, Zhiping
, p. 2026 - 2029 (2013/06/04)
An intermolecular oxidative cyclization between thiophenols and alkynes for benzothiophene formation has been established. A variety of multifunctional benzothiophenes are synthesized. In addition, we demonstrated that the obtained benzothiophenes can be
Synthesis of novel highly active thiophene and benzothiophene containing diphosphine ligands and their use in the asymmetric allylation of catechol
Tietze, Lutz F.,Lohmann, J. Klaas,Stadler, Christian
, p. 1113 - 1116 (2007/10/03)
Novel thiophene and benzothiophene containing diphosphine ligands 5-8 with a chiral cyclohexyl diamine backbone have been prepared and used in the asymmetric allylation of catechol. The advantage of these new ligands is their high reactivity and excellent
A New Indirect Application of Aggregative Activation: Synthesis of Esters by Cobalt-Catalyzed Carbonylation of Aryl, Heterocyclic, and Vinyl Halides under Atmospheric Pressure
Marchal, Joel,Bodiguel, Jacques,Fort, Yves,Caubere, Paul
, p. 8336 - 8340 (2007/10/02)
Sun lamp illuminated alkoxycarbonylation of aryl, heteroaryl, and vinyl halides was performed under atmospheric pressure of CO in the presence of a cobalt catalyst in situ generated from Co(OAc)2.Illunination through a Pyrex flask was sufficient to catalyze the reaction.This process avoids the use of Co2(CO)8 and excess CH3I, which were required in the earlier procedure.A SRN1 mechanism is proposed.
Anti-inflammatory and analgesic benzothiophene and benzafuran derivatives, compositions, and method of use therefor
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, (2008/06/13)
Compounds of formula (I): STR1 wherein: Ar is phenyl optionally substituted in the o-, m- or p-position by C1-4 alkyl, C1-4 alkoxy, trifluoromethyl, bromo, chloro or fluoro, pyrryl optionally N-substituted by C1-4 alkyl, 2-furyl or 2-thienyl either optionally substituted in the 3-, 4- or 5-position by methyl, chloro or bromo, or 3-furyl or 3-thienyl; X is oxygen, sulphur, sulphoxide or sulphone, Y is methylene, R1 and R3 are hydrogen or C1-4 alkyl, and R2 is hydrogen, C1-4 alkyl, fluoro, chloro or bromo, or X is methylene, Y is oxygen, R1 and R3 are both hydrogen, and R2 is hydrogen, fluoro, chloro or bromo; and R4 is hydrogen or C1-4 alkyl, or a salt thereof, have analgesic and/or anti-inflammatory activity.
alpha-Phenylpropionic Acid Derivatives. Synthesis and Dethiation of 5-Benzoylbenzothiophene-3-carboxylic Acid
Hannoun, Mohammad,Blazevic, Nikola,Kolbah, Dragutin,Mihalic, Mladen,Kajfez, Franjo
, p. 1131 - 1136 (2007/10/02)
The total synthesis of the title compound 8 started with p-thiocresol which was acylated with oxalyl chloride to give compound 1.This product underwent a condensation reaction with chloroacetic acid under basic conditions yielding compound 2.Two different synthetic pathways were used to convert compound 2 into the title compound 8.The first consisted in decarboxylation of 2 to 3, which was then converted to the ester 4, which was brominated and the product 5 was subjected to a Friedel-Craft's reaction with benzene.The resulting benzyl derivative 6 was oxidized to the benzoyl stage i.e. compound 7, which was finally hydrolyzed to 8.The second pathway was similar to the first one so that the steps of esterification, bromination, Friedel-Craft's alkylation and oxidation started with the dicarboxylic acid 2.Thus compounds 12-16 were obtained, and the last product was decarboxylated to 8.The yields in both procedures were similar.Finally, the dethiation of compound 8 with Raney nickel afforded compounds 18, 19 and 20.
Synthesis of Pyrano/Pyrido Benzothiophene Derivatives. Part-I
Chatterjea, J. N.,Sahai, Radhika P.
, p. 1372 - 1374 (2007/10/02)
A synthesis of 3-methoxycarbonylbenzothiophene-2-acetate and 2-formyl-3-methoxycarbonylbenzothiophene is reported.These key compounds have been converted into condensed heterocycles by standard methods.
