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

TitleCombined 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
Publication TypeJournal Article
Year of Publication2010
AuthorsRamana, CV, Patel, P, Vanka, K, Miao, B, Degterev, A
JournalEuropean Journal of Organic Chemistry
Issue31
Pagination5955-5966
Date PublishedNOV
ISSN1434-193X
KeywordsAnthranil, cyclization, Density functional calculations, isatogens, Nitro-alkyne cycloisomerization, Palladium
Abstract

Highly selective cycloisomerization of o-alkynylnitrobenzenes, leading to isatogens, has been achieved by employment of a Pd-II 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.

DOI10.1002/ejoc.201000769
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

3.206

Divison category: 
Organic Chemistry