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FeCl3–SiO2 promoted one-pot, three-component synthesis of novel.pdf

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FeCl3–SiO2 promoted one-pot, three-component synthesis of novel

ORIGINAL PAPER FeCl3–SiO2 promoted one-pot, three-component synthesis of novel 1,5-benzodiazepine derivatives Ying-Shuang An ? Xiao-Qing Li ? Xiao-Ran An ? Lan-Zhi Wang Received: 27 March 2014 / Accepted: 1 July 2014 Springer-Verlag Wien 2014 Abstract An efficient and simple synthesis of novel 4-methyl-2-(pyridin-2-yl)-2,5-dihydro-1,5-benzodiazepine- 3-carboxylate derivatives by one-pot, three-component reaction of substituted 1,2-phenylenediamines, 2-pyridine- carboxaldehyde, and b-keto ester in the presence of a catalytic amount of silica-supported FeCl3 (FeCl3–SiO2) is reported. The catalyst FeCl3–SiO2 was found highly active, robust, recovered, and reusable. The desired products were obtained in excellent yields and confirmed by IR, 1H NMR, 13C NMR, MS, and elemental analysis. Keywords 1,5-Benzodiazepine FeCl3–SiO2 One-pot synthesis Introduction 1,5-Benzodiazepines and their derivatives are important nitrogen-containing heterocyclic compounds due to diverse biological properties [1], such as anti-inflammatory, anti- anxiety, anticonvulsant, antidepressive, hypnotic, analgesic, sedative [2–5]. In addition, they are important intermediates for the preparation of fused ring derivatives; for example, triazolo-, oxadiazolo-, oxazino-, and furano- benzodiazepines [6–10]. The commercial applications of these compounds as dyes for acrylic fibers and in photog- raphy have also been reported [11–14]. Therefore, the research on synthesis method and biological activity of 1,5- benzodiazepines have become one of the hot issues. In the past decades, various catalysts were used to pre- pare 1,5-benzodiazepines, such as molecular iodine [15], NaBH4 [16], MgBr2 [17], Yb(OTf)3 [18], polyphosphoric acid [19], MgO/POCl3 [20], AcOH [21] and so on. How- ever, many of these conventional catalysts are associated with several shortcomings of low yields, long reaction time, drastic reaction conditions, occurrence of several side reactions, and the pollution of environments. Recentl