In the past decades, Multi-component reactions (MCRs) have been shown to be powerful tools for the synthesis of biologically active compounds and drug candidates from simple and readily accessible starting materials. 1 They offer significant advantages over conventional synthetic strategies by shortening reaction time, reducing waste, saving energy and making full use of starting materials. [2][3][4] Furthermore, the design of MCRs for the development of efficient chemical syntheses of complex and high added value molecules is another attractive area in chemistry. [5][6][7] Naphthoquinone derivatives particularly 3-substituted-2-hydroxy-1,4-naphthoquinones are of much importance because this fragment is a key moiety in numerous biologically active compounds. 8 For example as showed in the figure 1, atovaquone, lapachol, parvaquone and buparvaquone (Figure 1, first row) exhibit antimalarial, antibacterial, antiprotozoal, antitumor activities. 9 Similarly, pyrazolone framework is a well-known heterocycle in many drug substances of medicinal fields. To list some pyrazolone derivatives ( figure 1, seond row) such as antipyrine (phenazone), 4-aminopyrine (aminophenazone), metamizol (novalgin), and 4-isopropylpyrine (propyphenazone) are all useful antipyretic and analgesic drugs. 10 Pyrazolone derivatives also have ubiquitous applications in the development of acaricides, dyes, fungicides, herbicides, insecticides, inhibitors and reagents. [11][12][13][14][15][16][17] It is promising that the integration of these two bioactive units into a single molecule may exhibit new or improved pharmacological properties.Considering the above points, and also in continuation of our interest on the synthesis of different kinds of heterocyclic compounds based on MCRs. [18][19][20][21][22][23][24][25] Herein we wish to report MgCl 2 as a low-toxic catalyst for one-pot synthesis of 2-hydroxy-3-((5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(phenyl)methyl)naphthalene-1,4-dione

Key indicatorsSingle-crystal X-ray study T = 293 K Mean '(C±C) = 0.007 A Ê R factor = 0.045 wR factor = 0.088 Data-to-parameter ratio = 15.8For details of how these key indicators were automatically derived from the article, see

All of the reagents were purchased from Aldrich-reagent and used without further purifications. 1 H NMR spectra and 13 C NMR spectra were recorded on a Bruker Advance III 500 MHz spectrometer and using DMSO-d 6 (500 MHz for 1 H or 125 MHz for 13 C, respectively) as solvent. Chemical shifts of 1 H and 13 C NMR spectra were expressed in δ values (ppm) downfield from tetramethylsilane. Microanalyses were taken on a VARIOX Elemental Analyzer. Mass spectra were carried out on VARIAN1200. IR spectra were obtained on a TENSOR 27 spectrometer. Melting points were recorded on microscope (SGW X-4) melting point apparatus. The reaction was monitored by TLC. Experimental details and characterizationGeneral procedure for preparation of oxindole derivatives 3a-3p and 5a-5e A mixture of the isatin 1 or acenaphthenequinone 4 (1 mmol), indole 2 (2 mmol), p-TSA (10 mol %), CH 2 Cl 2 (10 mL) was added to 50 mL flask and stirred at room temperature until the the completion of the reaction (Scheme 1, 2). Then the solid was filtered and washed with CH 2 Cl 2 (5 mL) and ethanol (5 mL) in turns, affording the product in excellent yields, which was recrystallized from ethanol to produce pure crystalline products. The products were identified by elemental analysis, MS, 1 H NMR, 13 C NMR, and IR spectra. Scheme 1. Preparation of product 3a-3p Scheme 2. Preparation of product 5a-5e Spectroscopic and characterization data 3,3-di(1H-indol-3-yl)indolin-2-one (3a): Yield: 92%; white solid; m. p. 318-320 (lit. [26]

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An efficient mild one-pot synthesis of spiro [indoline-3,4'-pyrano[2,3-c]pyrazole derivatives by a four-component reaction of hydrazine, a β-keto ester, isatin, and malononitrile catalysed by L-proline in water is reported.

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An efficient synthesis of spiro [indoline-3,7′-pyrrolo[1,2-c]imidazole] is achieved through a three-component reaction of isatins, malononitrile, and hydantoin/2-thiohydantoin in water catalysed by NaHCO 3 . All the target compounds were screened for the Cell Division Cycle 25 Phosphatase B (CDC25B) inhibitory activities.