Three-component synthesis of quinolone derivatives
bearing 1,3-indandione moiety using pyridinium salts
Received: 12 August 2016 / Accepted: 8 November 2016 / Published online: 19 November 2016
Ó Springer Science+Business Media Dordrecht 2016
Abstract A series of 3,4-disubstituted dihydroquinolin-2(1H)-ones have been
synthesized via three-component reaction of 1,3-indandione with isatin derivatives
and N-phenacyl pyridinium bromide salts in presence of triethylamine as basic
reagent. This procedure affords a highly efﬁcient route for accessing quinolones by
ring expansion of isatin via a one-pot pathway. Products were obtained in good to
moderate yield without requiring a chromatographic puriﬁcation step.
Keywords Dihydroquinolin-2(1H)-ones Á 1,3-Indandione Á Isatin Á Pyridinium salts
3,4-Dihydroquinolin-2(1H)-ones have attracted attention from chemists and biol-
ogists because of their pharmaceutical activities such as phosphodiesterase
inhibitory , antiplatelet , and cardiovascular actions . Several routes have
been reported in literature for synthesis of these compounds [4–7]. One of the most
important approaches is ring expansion of isatin using different reagents, such as
diazomethane  or ethyl diazoacetate .
On the other hand, the 1,3-indandione motif is widely found in many natural
products with useful biological activities [10–12]. Also, its derivatives have been
employed in synthesis of potentially important compounds, such as drugs  and
dyes and pigments .
Electronic supplementary material The online version of this article (doi:10.1007/s11164-016-2808-0)
contains supplementary material, which is available to authorized users.
& Robabeh Baharfar
Department of Chemistry, University of Mazandaran, P. O. Box 47415, Babolsar, Iran
Res Chem Intermed (2017) 43:3007–3014