872415-26-4Relevant academic research and scientific papers
One-Pot Double-Annulation Strategy for the Synthesis of Unusual Fused Bis-Heterocycles
Abdul-Rashed, Shukree,Alachouzos, Georgios,Brennessel, William W.,Frontier, Alison J.
, p. 4350 - 4354 (2020)
A novel metal-free double-annulation cascade for the construction of unusual fused heterocyclic systems is described. This simple protocol enables the sequential assembly of two rings in one pot from two simple precursors. Acidic conditions promote the condensation and the intramolecular alkynyl Prins reaction of an enyne or arenyne alcohol with a cyclic hemiaminal to form a five-, six-, or seven-membered oxacycle followed by a seven-or eight-membered azacycle. In this transformation, chemical complexity is rapidly generated with the formation of three new bonds (one C-O, one C-C, and one C-N) in one synthetic operation. The strategy is modular and relatively general, providing access to a series of unique fused bicyclic scaffolds.
Synthesis of Spirocyclic Isoindolones Using an Alkynyl aza-Prins/Oxidative halo-Nazarov Cyclization Sequence
Hernandez, Jackson J.,Frontier, Alison J.
supporting information, p. 1782 - 1786 (2021/03/08)
In this report, we describe an alkynyl halo-aza-Prins cyclization of 3-hydroxyisoindolones to prepare aza-Prins products. These Prins adducts undergo oxidation at the 3-isoindolone position after activation of the amide by triflic anhydride and 2-chloropyridine to form a pentadienyl cation capable of undergoing a halo-Nazarov cyclization. Using this methodology, angular-fused N-heterocyclic small molecules with two new rings, two new carbon-carbon bonds, a vinyl halide, and an aza-tertiary stereocenter can be obtained in good yields.
Tetrahydroxydiboron-Promoted Radical Addition of Alkynols
Sun, Ze-Ying,Zhou, Sen,Yang, Kai,Guo, Minjie,Zhao, Wentao,Tang, Xiangyang,Wang, Guangwei
supporting information, p. 6214 - 6219 (2020/08/12)
Tetrahydroxydiboron has previously been used as a borylation or reducing reagent in organic synthesis. Herein, we present a novel tetrahydroxydiboron-promoted radical addition of internal alkynes followed by intramolecular oxidation of alcohol through 1,5-hydrogen atom transfer. Preliminary mechanistic studies showed that the process might be initiated through N,N-dimethylformamide-assisted homolytic cleavage of tetrahydroxydiboron. This process provides a convenient synthesis of fluoroalkyl-substituted alkenes with a pendant aldehyde or ketone moiety.
Leveraging the Halo-Nazarov Cyclization for the Chemodivergent Assembly of Functionalized Haloindenes and Indanones
Holt, Connor,Alachouzos, Georgios,Frontier, Alison J.
supporting information, p. 5461 - 5469 (2019/03/29)
In this report, we describe a halo-Prins/aryl halo-Nazarov cyclization strategy that employs readily available starting materials, inexpensive reagents, and convenient reaction procedures to generate functionalized haloindenes and indanones. The scope and
Indole derivatives comprising an acetylene group
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Page/Page column 22, (2008/06/13)
This invention is directed to compounds of the formula (I): wherein one of R6, R7, R8 and R9 is and X, R1 to R12, m, n and o are as defined in the description, and pharmaceutically acceptable salts and/or esters thereof. The invention is also directed to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are modulated by PPARδ and/or PPARα agonists.
Phenyl derivatives comprising an acetylene group
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Page/Page column 27, (2010/02/15)
This invention is concerned with compounds of the formula I: wherein one of R5, R6 and R7 is and X1, X2, R1 to R12, m, n and o are as defined in the description, and pharmaceutically acceptable salts and/or esters thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are modulated by PPARδ and/or PPARα agonists.
