3469-05-4Relevant academic research and scientific papers
Development and Application of O-(Trimethylsilyl)aryl Fluorosulfates for the Synthesis of Arynes
Chen, Qiao,Yu, Hongmei,Xu, Zhaoqing,Lin, Li,Jiang, Xianxing,Wang, Rui
, p. 6890 - 6896 (2015/10/06)
A class of o-(trimethylsilyl)aryl fluorosulfates was synthesized by a concise method and successfully used as aryne precursors for the first time. Different trapping agents such as azides, furans, and acyl acetoacetates could successfully react with the a
Arynes double bond insertion/nucleophilic addition with vinylogous amides and carbodiimides
Wu, Chao,Li, Ran,Tang, Huarong,Fu, Haixing,Ren, Hailong,Wang, Xuemei,Wu, Chunrui,Shi, Feng
, p. 1344 - 1355 (2014/03/21)
Arynes are shown to insert into some C=X double bonds, leading to benzannulated four-membered rings. The strain of these rings allow for a ready, spontaneous opening to afford o-quinomethide analogues. Subsequent nucleophilic addition re-aromatizes the intermediates to achieve ortho-difunctionalization of arynes. In this report, we describe the aryne insertion into the C=C double bonds of vinylogous amides and the C=N double bonds of carbodiimides. The correlation and comparison with aryne single bond insertion chemistry will be discussed. Computational studies for the ring-opening step, as well as the nature of the o-quinomethide intermediates, will also be discussed.
Reaction of arynes with vinylogous amides: Nucleophilic addition to the ortho-quinodimethide intermediate
Li, Ran,Wang, Xuemei,Wei, Zhibin,Wu, Chunrui,Shi, Feng
supporting information, p. 4366 - 4369 (2013/09/24)
The reaction of arynes with vinylogous amides containing no free N-H bonds proceeds in a [2 + 2] cycloaddition fashion at ambient temperature. The electronic properties of the vinylogous amides allow for the cycloadducts undergoing a facile ring-opening p
Design and application of new imidazolylsulfonate-based benzyne precursor: An efficient triflate alternative
Kovacs, Szabolcs,Csincsi, Adam I.,Nagy, Tibor Zs.,Boros, Sandor,Timari, Geza,Novak, Zoltan
supporting information; experimental part, p. 2022 - 2025 (2012/06/16)
Several o-(trimethylsilyl)aryl imidazolylsulfonates were synthesized in a simple process and successfully applied in cycloadditions involving benzyne intermediates. The precursor offers an efficient alternative for generating benzynes compared to widely used ortho TMS triflates under similar reaction conditions. With the utilization of this new precursor, the formation of potentially genotoxic trifluoromethanesulfonate side product is eliminated. The applicability of the new benzyne precursor was demonstrated in different types of cycloaddition reactions to prepare heterocyclic molecules.
A novel tandem [2 + 2] cycloaddition-Dieckmann condensation with ynolate anions. Efficient synthesis of substituted cycloalkenones and naphthalenes via formal [n + 1] cycloaddition
Shindo,Sato,Shishido
, p. 7818 - 7824 (2007/10/03)
A novel tandem [2 + 2] cycloaddition-Dieckmann condensation via ynolate anions is described. Ynolate anions are useful for the formation of reactive β-lactone enolates via a pathway not involving the enolization of the corresponding β-lactones. The [2 + 2] cycloaddition of ynolate anions with δ- or σ-keto esters, followed by Dieckmann condensation, gives bicyclic β-lactones, which are easily decarboxylated to produce synthetically useful 2,3-disubstituted cyclopentenones and cyclohexenones in one pot. This tandem reaction was applied to a novel, one-pot synthesis of highly substituted naphthalenes.
β-Lapachone: Synthesis of Derivatives and Activities in Tumor Models
Schaffner-Sabba, Karl,Schmidt-Ruppin, Karl H.,Wehrli, Walter,Schuerch, ALfred R.,Wasley, Jan W. F.
, p. 990 - 994 (2007/10/02)
In order to find a 3,4-dihydro-2H-naphthopyran-5,6-dione more potent than the naturally occurring 2,2-dimethyl derivative , we synthesized a series of analogous compounds with modifications at position 2 of the pyran ring or at positions 8 and 9 of the benzene ring.Of the compounds tested in vitro for inhibition of RNA-dependent DNA polymerase and in mice infected with Rauscher leukemia, all retained good enzyme activity.Inhibition of the reverse transcriptase activity of the 2,2-substituted derivatives 10b-e was as strong as 10a.However, only the 2-methyl-2-phenyl derivative 10e proved to be about as potent as 2,2-dimethyl reference compound 10a in prolonging the mean survival time of mice with Rauscher leukemia virus induced leukemia.
