Synthesis of 1,8-naphthyridines: a recent update (microreview)
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Synthesis of 1,8-naphthyridines: a recent update (microreview) Mahesh R. Kulkarni1, Nitin D. Gaikwad1* 1
Organic Chemistry Research Centre, Department of Chemistry, K.R.T. Arts, B. H. Commerce and A. M. Science College, Gangapur Road, Nashik 422 002, MS, India; е-mail: [email protected]; [email protected]
Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(8), 976–978
Submitted April 20, 2020 Accepted after revision May 23, 2020
This microreview focuses on the recent achievements (2015–2019) toward the synthesis of 1,8-naphthyridines, which include multicomponent reactions, Friedländer approach using green strategy, hydroamination of terminal alkynes followed by Friedländer cyclization, metal-catalyzed synthesis, and ring expansion reaction of 3-substituted 1H-pyrrolo[2,3-b]pyridin-2(3H)-one. Introduction 1,8-Naphthyridines have emerged as an important class of heterocyclic compounds due to their diverse biological activities1 and photochemical properties.2 Gemifloxacin, a compound containing 1,8-naphthyridine core has reached drug market for the treatment of bacterial infections3a and many more are under clinical investigations.3b Moreover, this class of heterocycles finds use as ligands5 and components of light-emitting diodes,4 dye-sensitized solar cells,6 molecular sensors,7 or self-assembly host–guest
systems.8 Due to the wide applicability in medicinal chemistry and materials science, the development of methods for the synthesis of 1,8-naphthyridines has been of considerable interest to synthetic community including attempts to develop more ecofriendly, safe, and atomeconomical approaches. Naphthyridine chemistry up to 2015 has been reviewed a few times.9–11 This review summarizes selected efforts toward the synthesis of 1,8-naphthyridines published since 2015.
Multicomponent reactions Multicomponent reaction (MCR) can efficiently generate a diverse set of complex molecular architectures which have wide application in medicinal chemistry and chemical biology. Therefore, chemical community has actively pursued to develop novel MCR or improve efficiency of existing MCR. Ghorbani-Vaghei et al. have constructed trisubstituted 2-amino-1,8-naphthyridines in moderate to high yield via MCR of substituted aromatic aldehydes, 2-aminopyridine, malononitrile or methyl or ethyl cyanoacetate in the presence of N,N,N',N'-tetrabromobenzene-1,3-disulfonamide (TBBDA) or poly(N,N'-dibromo-N-ethylbenzene-1,3-disulfonamide) (PBBS).12
Nitin D. Gaikwad obtained his PhD degree in chemistry from the Savitribai Phule Pune University in 2012. Currently, he serves as Associate Professor and Research Guide of the Doctoral Course in Chemistry at the K.R.T. Arts, B. H. Commerce and A. M. Science (K.T.H.M.) College, Nashik. His research interests include development of synthetic methodologies and medicinal chemistry.
Mahesh R. Kulkarni obtained his PhD in chemistry, from the Savitribai Phule Pune University in 2019 under supervision of Dr. Nitin D. Gaikwad. His current research interests include the develop
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