Dr. Suyog N. Korade
@unichemlabs.com
Research executive, Process Research department, Centre of Excellence,
Unichem Laboratories Ltd.
EDUCATION
M.Sc., SET, Ph.D. (Organic Chemistry)
Scopus Publications
Scopus Publications
Suyog N. Korade, Pradeep M. Mhaldar, Prafulladatta P. Kulkarni, Gajanan S. Rashinkar, and Dattaprasad M. Pore
Informa UK Limited
Abstract Meglumine, a biodegradable basic organo-catalyst has been efficiently explored for the one-pot synthesis of new fluorescent 2-amino-4-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-6-aryldiazenyl-4H-chromene-3-carbonitriles in an aqueous medium at room temperature. The synthesized compounds were found highly fluorescent when screened for photoluminescence properties. The planar structure equipped with substituted aryldiazenyl group led to the extension of conjugation that facilitated fluorescence emission in the visible region with a large stokes shift of 290–294 nm. The novelty of work is a synthesis of highly conjugated molecular assembly, high yield in shorter reaction time, energy efficiency, atom economy, utilization of water as a universal green solvent and meglumine as an eco-benign organo-catalyst. Graphical Abstract
Suyog N. Korade, Jayavant D. Patil, Deepak S. Gaikwad, Suraj A. Sonawane, Sandip P. Vibhute, Nilam C. Dige, Pradeep M. Mhaldar, and Dattaprasad M. Pore
Informa UK Limited
Interestingly, in some examples of bioactive heterocycles, a more pronounced effect is observed when two or more different heterocyclic moieties are incorporated within a single molecule. In this context, recent attention is focused on construction of structures with multiple heterocycles, as well as on the creation of heterocyclic diversity from common precursors. The benzopyran motif, for example, plays a vital role in pharmaceutical chemistry. The benzopyran core is considered to be responsible for most of significant biological activities such as Epicalyxin F exhibiting antiproliferative activity against HT-1080 fibrosarcoma and colon 26-L5 carcinoma, tetrahydrocannabinol possessing an agonistic effect on cannabinoid receptors, CB 1 and CB 2, and rhododaurichromanic acid A showing phytotoxic properties. Other valuable heterocycles, such as xanthenes and 5-deaza-10-oxaflavins also incorporate the benzopyran skeleton. In particular, 1-oxo-hexahydroxanthenes have such pharmacological properties as antibacterial, antiestrogenic, antithrombin and hypoglycemic activities. Like xanthenes, 5-deaza-10oxaflavins have received strong attention from organic chemists. They have been employed as intermediates for the preparation of other heterocycles as well as acting as selective organic oxidants under mild conditions. Moreover, they are known to display bioactivity as drugs. Such compounds have long been of interest because of their unique photochemical and photophysical properties. But they are also well known for their medicinal significance. Notably, they play a vital role in biological reactions such as the inhibition of DNA, RNA, carcinogenesis, protein synthesis and nitrogen fixation. Interestingly, some arylazo compounds are found to exhibit anti-HIV, anti-inflammatory and cytoprotective activities (Figure 1). In our own work, we hypothesized that, if benzopyran fused heterocycles were merged together with aryldiazo groups, the resulting molecular scaffolds might possess enhanced bioactivity. In continuation of our interest in ionic liquid catalyzed organic transformations, we report herein the synthesis of 1-oxo-hexahydroxanthenes, 5-deaza-10-oxaflavins, 2,3-dihydroquinazolin-4(1H)-ones and 1,2,4-triazolidine-3-thiones incorporating aryldiazo groups. This was accomplished using catalysis by the ionic
Suyog N. Korade and Dattaprasad M. Pore
Wiley
S.P. Vibhute, P.M. Mhaldar, S.N. Korade, D.S. Gaikwad, R.V. Shejawal, and D.M. Pore
Elsevier BV
Mansing M. Mane, Suyog N. Korade, Sarika M. Chinchkar, and Dattaprasad M. Pore
Informa UK Limited
A variety of condensation procedures have been used for the synthesis of chromenopyridine derivatives. Marta Costa reported a two component method for synthesis of 4amino-2-hydroxy-5-methylidene-5H-chromeno [3,4-c]pyridine-1-carbonitriles (4) from 2-oxo-2H-1-benzopyran-3-carbonitrile and cyanoacetamide in the presence of triethylamine, which were active at adenosine receptors. O’Callaghan and co-workers carried out the same reaction in presence of ammonium acetate. However, they observed formation of a different class of chromenopyridines by a ring opening mechanism. (Scheme 1). Although adenosine receptors 4 could be obtained by the former method, the yield was low (26–35%). To improve the yield, an efficient multi-component strategy is essential. The method presented in this study allows the synthesis of 4 from salicylaldehyde, ethyl cyanoacetate and ammonium acetate (Scheme 1). The multi-component reaction of salicylaldehyde, cyano ethylacetate and ammonium acetate in ethanol under reflux condition formed the expected product 4 in good yield. When the reaction was carried out in water at reflux, unexpected formation of ethyl-2-amino-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate (5) was observed (Scheme 1). This finding may be due to the affinity of the –CN group towards hydrogen bonding in water, increasing the electrophilicity of –CN. In either solvent, isolation of the product was carried out by simple filtration. The H NMR (DMSO-d6) spectrum of 4a (Table 1, entry 1) exhibited two singlets at d 8.98 ppm and d 8.39 (broad) ppm corresponding to –NH and –NH2 protons, respectively. In case of 5a, the presence of notable doublets at d 4.33 and 4.54 ppm with coupling constant 3.6Hz indicates the presence of a benzylic proton and methine proton, respectively. The C NMR spectrum of 4a depicted a signal at d 169 ppm indicate the presence of only one carbonyl carbon, while signals at d 80.60 and 86.64 ppm are due to the sp carbons of pyridine bearing –NH2 and –CN groups, respectively. In case of
Nilam C. Dige, Suyog N. Korade, and Dattaprasad M. Pore
Springer Science and Business Media LLC
D. S. Gaikwad, K. A. Undale, D. B. Patil, D. M. Pore, S. N. Korade, and A. A. Kamble
Springer Science and Business Media LLC
Sarika M. Chinchkar, Jayavant D. Patil, Suyog N. Korade, Gavisiddappa S. Gokavi, Rajendra V. Shejawal, and Dattaprasad M. Pore
Bentham Science Publishers Ltd.
Suyog N. Korade, Jayavant D. Patil, and Dattaprasad M. Pore
Springer Science and Business Media LLC
Pradeep B. Patil, Jayavant D. Patil, Suyog N. Korade, Siddheshwar D. Kshirsagar, Sanjay P. Govindwar, and Dattaprasad M. Pore
Springer Science and Business Media LLC
Jayavant D. Patil, Suyog N. Korade, Supriya A. Patil, Dipak S. Gaikwad, and Dattaprasad M. Pore
Royal Society of Chemistry (RSC)
A new task specific ionic liquid with hydroxyl and prolinate functionalities acts as a reducing agent and serves as a ligand and stabilizer for in situ formed palladium nanoparticles. This system displays high catalytic activity for Suzuki–Miyaura cross-coupling in water.
Jayavant D. Patil, Suyog N. Korade, and Dattaprasad M. Pore
Royal Society of Chemistry (RSC)
A novel and robust dication Brønsted acidic ionic liquid as a catalyst for the temperature influenced synthesis of novel pyranopyrimidinediones and pyranopyrimidinetriones.