5
key features of our methodology, which gives the simple and
rapid access to the titled compounds which are of great interest in
the medicinal and pharmaceutical chemistry.
To check the scope of this methodology isatin (5) was used as
the electrophile and treated with quinaldine to isolate 3,3-
bis(quinolin-2-ylmethyl)indolin-2-one (6a) in 73% yield after 24
h (Scheme 4). Similarly quinaldine 2d also reacted with isatin to
furnish 70% of 6b after 24 h. When 2-methylpyridine 1b was
used as the nucleophile against isatin we could not see the
expected product even after 48 h but the formation of
intermediate alcohol 3-hydroxy-3-(pyridin-2-ylmethyl)indolin-2-
one (7) was observed (entry 8, Table 3).
Acknowledgments
SY acknowledge DST-India, for their financial support. GS
and RD thank Central University of Rajasthan and CSIR for their
fellowships respectively.
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In summary, we have developed a mild, efficient and
sustainable catalytic system for the sp3 C-H functionalization of
methyl azaarenes. Biologically important (E)-2-styryl azaarenes,
3,3-bismethyl azaarenyl indolinones and 2-aryl-1,3-bisazaarenes
have been synthesized in excellent yields using simpler reaction
conditions. Use of environmentally benign and inexpensive
catalyst, step economy, solvent-free conditions (for styryl
azaarenes), high yields and substrate diversity are some of the