Diversity oriented synthesis of pyrrolidines via natural carbohydrate solid acid catalyst.

Natural carbohydrate scaffold catalyzed diastereoselective synthesis of functionalized pyrrolidines have been developed via 1,3-dipolar cycloaddition of azomethine ylides derived from alpha-imino esters with dienes or dipolarophiles. Naturally most abundant carbohydrates, like cellulose and starch, were converted into their sulfuric acid derivative, which are exhibiting efficient catalytic properties, along with excellent cost effectivity and recyclability. The advantages of this methodology are diversity oriented metal free synthesis of functionalized pyrrolidines, mild reaction condition, high diasteroselectivity and yield.

Artificial sugar saccharin and its derivatives: role as a catalyst.

The primary objective of this review was to demonstrate the significance of artificial sugar saccharin and its derivatives as catalysts for a wide variety of organic transformations. The application of saccharin and its derivatives represents a greener and superior catalytic approach for reactions. In particular, we were interested in bringing together the literature pertaining to these saccharin derivatives from a catalysis perspective. The present review reports synthesis of saccharin and its derivatives such as saccharin-N-sulfonic acid, sodium saccharin, N-halo saccharin, saccharin lithium-bromide, N-formyl saccharin, N-acyl saccharin, N-nitrosaccharin, N-SCF3 saccharin, N-fluorosultam, N-phenylselenosaccharin, N-thiocyanatosaccharin palladium saccharin, DMAP-saccharin, and [Bmim]Sac. This catalytic application of saccharin and its derivatives includes reactions such as the Biginelli reaction, Paal-Knorr pyrrole synthesis, azo-coupling reaction, halogenations, domino Knoevenagel, Michael, deoximation reaction, catalytic condensation, functional group protection and oxidation etc. Also, these saccharin derivatives act as a source of CO, NH2, SCN, SCF3 and nitro groups. We reported all the available data on saccharin and its derivatives acting as a catalyst from 1957 to date.

Development of a fused imidazo[1,2-a]pyridine based fluorescent probe for Fe3+ and Hg2+ in aqueous media and HeLa cells.

A new fluorescent sensor 5 based on a fused imidazopyridine scaffold has been designed and synthesized via cascade cyclization. The reaction features the formation of three different C-N bonds in sequence. Imidazopyridine based fluorescent probe 5 exhibits highly sensitive and selective fluorescent sensing for Fe3+('turn-on') and Hg2+('turn-off'). The excellent selectivity of imidazopyridine for Fe3+/Hg2+ was not hampered in the presence of any of the competing cations. The limit of detection (LOD) of 5 toward Fe3+ and Hg2+ has been estimated to be 4.0 ppb and 1.0 ppb, respectively, with a good linear relationship (R 2 = 0.99). Notably, 5 selectively detects Fe3+/Hg2+ through fluorescence enhancement signalling both in vitro and in HeLa cells.

Anion-cation co-operative catalysis by artificial sweetener saccharine-based ionic liquid for sustainable synthesis of 3,4-dihydropyrano[c]chromenes, 4,5-dihydropyrano[4,3-b]pyran and tetrahydrobenzo[b]pyrans in aqueous medium.

In this study, a saccharine-based ionic liquid [Bmim]Sac has been found to be a sustainable catalyst for the synthesis of 3,4-dihydropyrano[c]chromenes, 4,5-dihydropyrano[4,3-b]pyran and tetrahydrobenzo[b]pyrans scaffolds through Domino Knoevenagel-Michael reaction. The easy recovery of the catalyst and high yield of the products make the protocol attractive, sustainable and economical. A mechanistic hypothesis is discussed using the concept of cooperative catalysis based on the dual (electrophilic/nucleophilic) activation of reactants by [Bmim]Sac. Furthermore, dual hydrogen bonding of saccharinate anions plays an important role in the activation of nucleophiles.

Betaine mediated synthesis of annulated dihydrofurans from oxobis(methylthio)ketene acetals and N-butyl-N'-methyl ethane-1,2-diamine as precursors via NHC elimination.

First in situ generation of a betaine intermediate has been developed using two new precursors oxobis(methylthio)ketene acetals and N-butyl-N'-methyl ethane-1,2-diamine for the synthesis of annulated dihydrofurans. This protocol adds a new dimension for the formation of annulated dihydrofurans through a series of selective consecutive formation of C-C and C-O bonds after reacting with enone rings. This in situ generated betaine intermediate corresponds to deoxy-Breslow intermediates in the reaction via elimination of NHC.

Synthesis of new class of alkyl azarene pyridinium zwitterions via iodine mediated sp3 C-H bond activation.

An efficient and conceptually different approach toward C-H bond activation by using iodine mediated sp(3) C-H functionalization for the synthesis of alkyl azaarene pyridinium zwitterions is described. This work has the interesting distinction of being the first synthesis of a new class of alkyl azaarene pyridinium zwitterion via transition-metal-free sp(3) C-H bond activation of an alkyl azaarene.

Natural product inspired diversity oriented synthesis of tetrahydroquinoline scaffolds as antitubercular agent.

An efficient natural product inspired diversity oriented syn thesis of tetrahydroquinoline analogues has been developed using the natural carbohydrate derived solid acid catalyst via multicomponent aza-Diels-Alder reaction of imine (generated in situ from aromatic amine and aldehyde) with dienophile in acetonitrile in a diastereoselective manner. The use of water as solvent reverses the diastereoselectivity toward the cis isomer. Interestingly, tricyclic pyrano/furano benzopyran with cis diastereoselectivity is obtained when salicylaldehyde is used as an alternative of aromatic aldehyde under the same condition. These synthesized quinolines and benzopyrans analogues have been evaluated for their Antitubercular activity against M. tuberculosis H37Ra, and M. tuberculosis H37Rv, and some of the analogues shows better activity profile than their natural product analogues. The protocol is not only mild, efficient, ecofriendly, but also involves reusable and biodegradable catalyst and provides route for both the diastereoisomer.