ISC, DOAJ, CAS, Google Scholar......

Document Type : Research Paper


Department of Chemistry, College of Chemical engineering , Mahshahr Branch, Islamic Azad University, Mahshahr, Iran


Abstract: The reactive 1:1 intermediate produced in the reaction between cyclohexyl isocyanide and electron- deficient acetylenic esters or dimethyl acetylene dicarboxylate was trapped by 2-cyano-N-(Aryl) acetamides to provides highly functionalized oxopyridine (potential synthetic and pharmaceutical interest )  in  acetonitrile under mild reaction conditions at ambient temperature after 24 h in fairly good yields. The structures of the products were corroborated spectroscopically (IR, 1H- and 13C-NMR),  by EI - MS, and elemental analysis. A possible mechanism for this reaction is proposed. This present method carries the advantage that not only is the reaction performed under neutral conditions, but also the substances and reagents  can be mixed without any modification or activation. The simplicity of this procedure and use of simple starting materialsmakes it an interesting alternative to other approaches.


[1]. Multicomponent Reactions; Zhu J, Bienayme´ H, Eds.; Wiley-VCH: Weinheim, 2005.
[2]. Basso A, Banfi L, Riva R, Guanti G, J Org Chem., 2005, 70, 575.
[3]. Ramo´n D J, Yus M, Angew Chem Int Ed., 2005, 44, 1602.
[4]. Do¨mling A, Chem Rev., 2006, 106, 17.
[5]. Do¨mling A, Ugi I, Angew Chem Int Ed., 2000, 39, 3169.
[6]. Anary-Abbasinejad M, Mosslemin M H, Anaraki-Ardakani H, Tahan S, J Chem Res., 2006, 306.
[7]. Yavari I, Anary-Abbasinejad M, Alizadeh A, Hossaini Z, Tetrahedron, 2003, 59, 1289.
[8]. Yavari I, Djahaniani H, Nasiri F, Tetrahedron, 2003, 59, 9409.
[9]. Anary-Abbasinejad M, Anaraky-Ardakani H, Rastegari F, Hassanabadi A, J Chem Res., 2007, 602.
[10]. Anary-Abbasinejad M, Mosslemin M H, Tahan S, Anaraki-Ardakani H, J Chem Res., 2006, 170.
[11]. Mosslemin M H, Anary-Abbasinejad M, Anaraki-Ardakani H, Synlett, 2009, 16, 2676.
[12]. Anaraki-Ardakani H, Mosslemin M H, Anary-Abbasinejad M, Shams N, Mirhosseini S H, Arkivoc, 2010, (xi), 343.
[13]. Mosslemin M H, Mohebat R, Barazandeh-Doust M, Anaraki-Ardakani H, J Chem Res., 2010, 228.
[15]. Yavari I, Anary-Abbasinejad M, Alizadeh A, Monatsh Chem., 2002, 133, 1221.
[16]. Ugi I, Angew Chem Int Ed Eng., 1982, 21, 810.
[17]. Walborsky H M, Periasamy M P, In The Chemistry of Functional Groups, Suppl C, Patai S, Rappoport Z, Eds. Wiley, New York., 20, 835, 1983.
[18]. Marcaccini S, Torroba T, Org Prep Proced Int., 1993, 25, 41.