A combined experimental and density functional theory study on the Pd-mediated cycloisomerization of o-alkynylnitrobenzenes - synthesis of isatogens and their evaluation as modulators of ROS-mediated cell death

Ramana, Chepuri V. ; Patel, Pitambar ; Vanka, Kumar ; Miao, Benchun ; Degterev, Alexei (2010) A combined experimental and density functional theory study on the Pd-mediated cycloisomerization of o-alkynylnitrobenzenes - synthesis of isatogens and their evaluation as modulators of ROS-mediated cell death European Journal of Organic Chemistry, 2010 (31). pp. 5955-5966. ISSN 1434-193X

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/ejoc.20...

Related URL: http://dx.doi.org/10.1002/ejoc.201000769

Abstract

Highly selective cycloisomerization of o-alkynylnitrobenzenes, leading to isatogens, has been achieved by employment of a Pd complex. This reaction is very general and functional-group-tolerant. The possible mechanism of this reaction was investigated with the help of DFT calculations. Three possible pathways – namely, the addition of the nitro group either in (i) 5-exo-dig or (ii) 6-endo-dig mode and (iii) halopalladation – and subsequent intramolecular events have been considered and studied in detail. These investigations revealed that pathway (i) is the favored route to isatogen formation. A preliminary screening of the available isatogens reveals the 2-alkylisatogens to be novel ROS scavengers capable of inhibiting cellular necroptosis.

Item Type:Article
Source:Copyright of this article belongs to John Wiley & Sons, Inc.
Keywords:Nitro–Alkyne Cycloisomerization; Cyclization; Palladium; Isatogens; Anthranil; Density Functional Calculations
ID Code:106016
Deposited On:01 Feb 2018 16:54
Last Modified:01 Feb 2018 16:54

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