Abstract
Graphene based magnetic nanohybrids have engrossed considerable research curiosity because of their exceptional properties and diverse applications associated with green chemistry. In this regard, a practical, facile and regioselective preparation of 1,2-diamines from N-tosylaziridine/(S)-(+)-2-Benzyl-1-(p-tolylsulfonyl)aziridine and aryl amines in the presence of magnetically separable graphene based nanohybrid (CoFe@rGO) has been proposed under mild and solvent free conditions. The FT-IR, FE-SEM, XPS, XRD and TEM spectroscopic analysis confirmed the formation of the CoFe@rGO nanohybrids. For unsymmetrical aziridine, nucleophilic attack of aryl amines was observed to take place selectively at the more substituted carbon atom of aziridine ring. Environmentally benign, efficient, shorter reaction time, solvent-free conditions, low catalyst loading, excellent reaction yields and reusability of the catalyst for six consecutive runs without significant loss in its activity are the key advantages of this protocol.Graphical Abstract
Highlights
Sulfonamides are a significant class of compounds displaying a wide variety of biological activities such as anti-fungal, anti-bacterial, anti-thyroid, anti-inflammatory and anti-viral etc. (Fig. 1) [1]
CoFe@reduced Graphene oxide (rGO) nanohybrid has been utilized as promising heterogeneous catalyst for the one step construction of benzensulfonamides derivatives via ring opening reaction of N-Tosylaziridine and (S)-(+)-2-Benzyl-1-(p-tolylsulfonyl) aziridine with different aromatic amines under solvent free conditions
The spectra of CoFe@rGO nanohybrid shows all the characteristic peaks of graphene oxide (GO), except the peaks around 1625–1725 cm− 1 and 1150 cm− 1 corresponding to the oxygen containing functional groups, which clearly indicates the complete reduction of GO to rGO
Summary
Sulfonamides are a significant class of compounds displaying a wide variety of biological activities such as anti-fungal, anti-bacterial, anti-thyroid, anti-inflammatory and anti-viral etc. (Fig. 1) [1]. The exploration of such protocol which is energy efficient, environmentally benign, facile, solvent free, and apparently separable are the current need of hour for the ring opening of aziridines In this regard, nano catalysis, which involves nanoparticles as heterogeneous catalysts has came to the forefront for carrying out various organic transformations in an environmentally benign manner. Carbon nanomaterials, in particular, the ones based on graphene have acquired enormous attention from material science and catalysis chemists; as a viable catalyst to carry out several organic transformations Amongst these materials, reduced Graphene oxide (rGO), has emerged as an excellent heterogeneous catalyst, because of its remarkable characteristics such as large specific surface area, high thermal stability, exceptional structural and electronic properties. CoFe@rGO nanohybrid has been utilized as promising heterogeneous catalyst for the one step construction of benzensulfonamides derivatives via ring opening reaction of N-Tosylaziridine and (S)-(+)-2-Benzyl-1-(p-tolylsulfonyl) aziridine with different aromatic amines under solvent free conditions. As compared to other conventional catalysts, CoFe@rGO nanohybrid exhibited better stability, negligible leaching, good recyclability, and no deactivation of the nanohybrid catalyst
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