ORIGINAL PAPER One-pot, three-component reaction of isocyanides, dialkyl acetylenedicarboxylates, and non-cyclic anhydrides: synthesis of 2,5-diaminofuran derivatives and dialkyl (E)-2-[(N-acyl-N-alkylamino)carbonyl]-2-butenedioates Mohammad Bayat • Hossein Imanieh • Nader Zabarjad Shiraz • Mohammad Shah Qavidel Received: 17 March 2009 / Accepted: 20 January 2010 / Published online: 27 February 2010 Ó Springer-Verlag 2010 Abstract Isocyanides, dialkyl acetylenedicarboxylates, and non-cyclic anhydrides, for example acetic anhydride or benzoic anhydride, react in one-pot to afford 2,5-diaminofu- ran derivatives and dialkyl (E)-2-[(N-acyl-N-alkylamino) carbonyl]-2-butenedioates in fairly good yields at room temperature. Keywords Isocyanides Á Acetylenic ester Á Acetic anhydride Á Multicomponent reaction Introduction Multicomponent reactions are well established as a pow- erful tool for rapid construction of complex and structurally diverse compounds from relatively simple building blocks [1–3]. Simple procedures, high atom-economy, chemical efficiency, and convergence are typical features of such one-pot condensations of at least three different starting materials. Because of the remarkably high purity of librar- ies, multicomponent reactions are well-suited for both combinatorial chemistry and high-speed parallel synthesis, and therefore have high exploratory power [4, 5]. Isocya- nide-based [6–10] multicomponent reactions, especially, have been emerging fields of interest in the last decade, but the construction of heterocycles via multicomponent reac- tions has also attracted interest recently [11–14]. Polysubstituted furans play an important role in organic chemistry, not only because of their presence as key structural units in many natural products [15] and in important pharmaceuticals [16] but also because of their use in synthetic chemistry as building blocks. For this reason the synthesis of polysubstituted furans continues to attract the interest of many synthetic chemists. Although the trapping of the 1:1 intermediate formed between dialkyl acetylenedicarboxylates and isocyanides with aldehydes [17], aromatic anhydrides [18, 19], 1,3- diones [20], benzoyl chlorides [21], benzoyl cyanides [22], quinones [23], malimide, and succinimides [24] has been studied in detail by a number of research groups [6–10], trapping of the initial 1:1 intermediate formed with acetic or benzoic anhydride has not been reported. Dimethyl acetylenedicarboxylate (DMAD) and isocya- nides undergo a variety of cycloadditions with a third component containing a carbonyl group to form diverse heterocyclic scaffolds. For example the reaction of DMAD, an isocyanide, and phthalic anhydride derivatives produces benzofused spirolactones [18, 19]. We planned to test a similar reaction between DMAD, isocyanide, and acetic anhydride or benzoic anhydride for construction of iminolactone derivatives, which was also based on the work of Esmaili and Bodaghi [18] and Shaabani et al. [19]. In these experiments we found that the reaction was different. We now report a simple one-pot synthesis of 2,5-diaminofuran derivatives and highly functionalized enone compounds using alkyl isocyanides 1 and dialkyl acetylenedicarboxylates 2 in the presence of acetic anhydride (3a) or benzoic anhydride (3b) as trapping agents for the reactive zwitterionic intermediate. This three-component condensation reaction produces highly functionalized compounds 4 and 5 in fairly good yields (Scheme 1). M. Bayat (&) Á H. Imanieh Á M. S. Qavidel Department of Chemistry, Imam Khomeini International University, Qazvin, Iran e-mail: bayat_mo@yahoo.com N. Z. Shiraz Department of Chemistry, Islamic Azad University, Tehran, Iran 123 Monatsh Chem (2010) 141:333–338 DOI 10.1007/s00706-010-0257-9