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A highly efficient triflic acid catalyzed ring opening of a wide variety of 1-cyclopropyl-2-propyn-1-ols with alcohols as an efficient synthetic route to conjugated enynes is reported. The mechanism involved protonation of the alcohol substrate by the TfOH catalyst, followed by ionization of the starting material to causes ring opening of the cyclopropane moiety and trapping by the alcohol nucleophile to yield the conjugated enyne product.

An efficient silvertriflate-catalyzed tandem hydroamination/hydroarylationcascade generating 1′-allylspiro[indene-1,2′-indolin]-3′-onesfrom 1-(2-allylamino)phenyl-4-hydroxy-but-2-yn-1-onesis described. The reaction conditions are mild and general in scopeand proceed to highly functionalized spiro-targets in high yield.This novel class of molecule possesses both the privileged indeneand indolin-3-one scaffold, which may lead to possible pharmacologicalapplications. [ABSTRACT FROM AUTHOR]

A method to prepare 1H-indole-2-carbaldehydes and (E)-2-(iodomethylene)indolin-3-ols by gold(I)-catalyzed cycloisomerization of 1-(2-(tosylamino)phenyl)prop-2-yn-1-ols with N-iodosuccinimide (NIS) is reported. The reactions were shown to be operationally simplistic and proceed efficiently for a wide variety of substrates, affording the corresponding products in good to excellent yields (70-99%). The mechanism is suggested to involve activation of the alkyne moiety of the substrate by the gold(I) catalyst. This triggers intramolecular addition of the tethered aniline moiety to give a vinyl gold intermediate, which undergoes iododeauration with NIS to give the (E)-2-(iodomethylene)indolin-3-ol adduct. Subsequent 1,3-allylic alcohol isomerization (1,3-AAI) followed by formylation of this vinyl iodide intermediate then gives the 1H-indole-2-carbaldehyde. [ABSTRACT FROM AUTHOR]

Aqueous organic redox flow batteries (AORFBs) have received considerable attention for large-scale energy storage. Quinone derivatives, such as 9,10-anthraquinone-2,7-disulphonic acid (2,7-AQDS), have been explored intensively owing to potentially low cost and swift reaction kinetics. However, the low solubility in pH-neutral electrolytes restricts their application to corrosive acidic or caustic systems. Herein, the single molecule redox-targeting reactions of 2,7-AQDS anolyte are presented to circumvent its solubility limit in pH-neutral electrolytes. Polyimide was employed as a low-cost high-capacity solid material to boost the capacity of 2,7-AQDS electrolyte to 97 Ah L -1 . Through in situ FTIR spectroscopy, a hydrogen-bonding mediated reaction mechanism was disclosed. In conjunction with NaI as catholyte and nickel hexacyanoferrate as the catholyte capacity booster, a single-molecule redox-targeting reaction-based full cell with energy density up to 39 Wh L -1 was demonstrated., (© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

The retinoic acid receptor-related orphan nuclear receptor γt (RORγt), a promising therapeutic target, is a major transcription factor of genes related to psoriasis pathogenesis such as interleukin (IL)-17A, IL-22, and IL-23R. On the basis of the X-ray cocrystal structure of RORγt with 1a , an analogue of the known piperazine RORγt inverse agonist 1 , triazolopyridine derivatives of 1 were designed and synthesized, and analogue 3a was found to be a potent RORγt inverse agonist. Structure-activity relationship studies on 3a , focusing on the treatment of its metabolically unstable cyclopentyl ring and the central piperazine core, led to a novel analogue, namely, 6-methyl- N -(7-methyl-8-(((2 S ,4 S )-2-methyl-1-(4,4,4-trifluoro-3-(trifluoromethyl)butanoyl)piperidin-4-yl)oxy)[1,2,4]triazolo[1,5- a ]pyridin-6-yl)nicotinamide ( 5a ), which exhibited strong RORγt inhibitory activity and a favorable pharmacokinetic profile. Moreover, the in vitro and in vivo evaluation of 5a in a human whole-blood assay and a mouse IL-18/23-induced cytokine expression model revealed its robust and dose-dependent inhibitory effect on IL-17A production., Competing Interests: The authors declare no competing financial interest., (Copyright © 2020 American Chemical Society.)

Don't cross me! 2-Alkynyl indoles were prepared efficiently by the AgOTf-catalyzed tandem heterocyclization/alkynylation of 1-(2-tosylamino)aryl)but-2-yne-1,4-diols under mild conditions (see scheme). The attractiveness of this approach lies in the fact that both the indole ring and alkyne side chain of the N-heterocycle are sequentially formed from low cost, readily available, and ecologically benign starting materials. It also provides the first route to this synthetically valuable class of compounds that is not based on a cross-coupling strategy., (Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)