Heteroatom Chemistry Volume 14, Number 5, 2003 Conversion of 2(3H )-Furanones Bearing Indole Nuclei Into Novel Amide, Pyrrolone, and Imidazole Derivatives Abdel-Sattar S. Hamad Elgazwy, 1 H. T. Zaky, 2 M. I. Mohamed, 2 H. M. Ahmed, 2 and N. G. Kandile 2 1 Department of Chemistry, Faculty of Science, University of Ain Shams, Abbassia 11566, Cairo, Egypt 2 Department of Chemistry, Faculty of Girls, University of Ain Shams, Heliopolis 11757, Cairo, Egypt Received 3 March 2003; revised 16 March 2003 ABSTRACT: 2(3H)-Furanones 1a–d having exo- cyclic double bond and N-acetylisatin nucleus were converted into the corresponding novel amides, pyrrolones, and imidazoles via nitrogen nucle- ophiles. All purposed structures were confirmed by NMR, mass spectra GC/MS, and chemical evi- dence. C  2003 Wiley Periodicals, Inc. Heteroatom Chem 14:434–442, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10175 INTRODUCTION Nitrogen heterocycles constitute an important class of natural and nonnatural products many of which exhibit useful biological activity [1–4]. Isatin, and a number of its derivatives, posses a reactive keto- carbonyl group that readily undergoes condensation reactions under mild conditions [5]. It was there- fore speculated that isatin would be a suitable elec- trophilic component for the Baylis–Hillman reaction Correspondence to: Abdel-Sattar S. Hamad Elgazwy, Group de Quimica Organometalica, Departamento de Quimica Inorgan- ica, Facultad de Quimica, Universidad de Murcia, Aptdo. 4021, E-30071 Murcia, Spain; e-mail: abhamad@um.es. Contract grant sponsor: Ain Shams University, Egypt. Contract grant number: EG-SHAMS-2, 2003. c  2003 Wiley Periodicals, Inc. [6] and a precursor for the synthesis of other het- erocycles [5,7–9]. Substituted isatins are found in plants, melosatin alkaloids can be obtained from the caribbean tumorigenic plant Melochia tomen- tosa [10–12], as well as in fungi, 6-(3 ′ -methylbuten- 2 ′ -yl)isatin was isolated from Streptomyces albus [13] and 5-(3 ′ -methylbuten-2 ′ -yl)isatin from Chaetomium globosum [14]. The interest in isatin derivatives stems from their pharmacological [15–16] and in- dustrial application [17,18]. RESULTS AND DISCUSSION The preparation of (3 E)-1-acetyl-3(5-aryl-2-oxofur- an-3(2 H)-ylidene)-1,3-dihydro-2 H-indol-2-ones 1a– d has already been described [19] as part of our previous investigation on 2-(3 H)-furanones [20–24]. These form only as E-isomers. This is consistent with the result described by Long et al. who stud- ied monosubstituted 3-methyleneoxindoles and de- tected for most of them only the E-isomer [25]. In this paper we examine the reactivity of 1a–d toward some nitrogen nucleophiles. N-Acetylisatin derivatives 1a–d were treated with anthranilic acid and o-phenylenediamine under different conditions (Scheme 1). With anthranilic acid in refluxing acetic acid, ring opening occurs with the formation of the E-isomers of amides 2a–d in 59–78% yield (i). This 434