Premium
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 (Eur. J. Org. Chem. 31/2010)
Author(s) -
Ramana Chepuri V.,
Patel Pitambar,
Vanka Kumar,
Miao Benchun,
Degterev Alexei
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201090085
Subject(s) - cycloisomerization , chemistry , electrophile , alkyne , aryl , alkyl , stereochemistry , medicinal chemistry , combinatorial chemistry , catalysis , organic chemistry
The cover picture shows the historical details of the nitro–alkyne cycloisomerization leading to isatogens. Since the first documentation of this reaction by Baeyer (picture of Baeyer and the corresponding literature citation are shown) in the late 19th century, a mild and general method for the synthesis of isatogens has been sought. The electrophilic Pd II halide complexes are found to bring about this cyclization to provide the desired isatogens and accommodate both aryl and alkyl substituents as well as tolerate commonly employed protecting groups/functional units. Details of the course of the reaction through advanced theoretical studies and the utility of isatogens as new ROS (reactive oxygen species) scavengers are discussed in the article by C. V. Ramana, K. Vanka, A. Degterev et. al. on p. 5955 ff.