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Nanorod-Shaped Basic Catalyzed N,N-Diformylation of Bisuracil Derivatives: A Greener “NOSE” Approach

DOI: 10.1155/2013/793159

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Abstract:

A feasible “NOSE” (nanoparticles-catalyzed organic synthesis enhancement) protocol has been developed for N,N-diformylation of bisuracil derivatives using nano-Al2O3 rods as an efficient, inexpensive, and recyclable catalyst under solvent-free reaction condition at 40°C. The catalyst was reused up to the 4th cycle without affecting the rate and yield of the N,N-diformylation products appreciably. 1. Introduction The exercise of metal/metal oxide nanoparticles as a frontier between the homogeneous catalysis and heterogeneous catalysis [1] in organic synthesis has invoked tremendous interests [2] in the recent times. The interesting features inherited with these small particle sizes are their large surface area along with more edges and corners and distinct electronic, optical, magnetic, thermal, and chemical properties [3–5]. The crucial role of nanoparticles in organic transformations is their excellent catalytic activity, straightforward recoverability, better selectivity, criteria of evolution, and their versatile role in green chemistry [6–10]. Thus, the domain of metal nanoparticle catalysis [11–13] should offer opportunities for mining new chemical reactions [14–16] which include the synthesis of biologically important and synthetically challenging natural products. In the context of green chemistry [17], organic synthesis in solvent-free reaction condition [18–21] has occupied a significant position in the recent years since solvent-free reaction condition involves the best reaction medium with “no medium” [22]. One of the key motifs present in the biopolymer RNA [23–26] is uracil, a nucleobase of the pyrimidine family which participates in various functions in our life processes [27]. Uracil derivatives also have several potent medicinal properties such as bronchodilators and anticancer [28, 29], antiallergic [30, 31], antiviral [32, 33], antihypertensive, and adenosine receptor antagonists [34, 35]. Recently, our research group reported a greener protocol for the synthesis of bisuracil derivatives [36]. Bisuracil and their analogues have also been isolated from marine sea hare Dolabella auricularia [37]. Some of the N-substituted bisuracil analogues have been screened for bioactivities against several diseases [38]. To explore the possible applications of the metal/metal oxide nanoparticles in organic synthesis, we have been focusing on the advancement of a protocol termed “NOSE” (nanoparticles-catalyzed organic synthesis enhancement) [39–41] chemistry in our laboratory. To the best of our knowledge, there has been no report on nano-rod-shaped

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