ORIGINAL PAPER Synthesis and characterization of some novel 4-arylglyoxal- chromene derivatives in the presence of a polymeric catalyst and biological evaluation against Escherichia coli Nader Ghaffari Khaligh 1,2 Received: 16 August 2016 / Accepted: 11 September 2017 / Published online: 1 December 2017 Ó Springer-Verlag GmbH Austria 2017 Abstract A poly(N-vinylimidazole)-catalyzed one-pot multicomponent reaction for the synthesis of 2-amino-4H- benzo[g]chromenes containing acyl group on the 4H- chromene ring has been developed. The products were obtained in generally good to excellent yields in the pres- ence of low loading of poly(N-vinylimidazole) as a reusable basic catalyst via this synthetic strategy. Impor- tantly, the catalyst has the unique ability of being easily separated and recycled. The products were screened for their antibacterial activity against Escherichia coli. The results of antibacterial studies showed that three 4-aroyl- chromene derivatives completely inhibited E. coli at 32 mg cm -3 , whereas other derivatives were either mod- erately active or inactive up to 64 mg cm -3 . Highest antimicrobial activity was observed when the phenylgly- oxal hydrate was substituted with fluoro, nitro, and methoxy groups at para position. Graphical abstract O O OH + O H Ar O + CN CN PVIm (50 mg) EtOH, reflux, 2 h O O Ar CN NH 2 O O Keywords 4-Aroylchromenes Á Antibacterial Á Escherichia coli Á Heterogeneous catalysis Á One-pot three-component reaction Introduction One-pot multicomponent reactions have received consid- erable attention in synthetic chemistry as they can produce desired products in a single step from three or more available reactants without the isolation of the intermedi- ates or exposure of toxic intermediates to environment; thus the synthesis can be performed within a short reaction time with reducing labor cost and waste production [1–5]. The 4H-chromone structural unit is widely observed in natural oxygen-containing heterocyclic compounds [6]. They exhibit various biological and pharmacological activities that depend on the nature of substituents either on the 4H-pyran or the adjacent rings [7–15]. A number of 2-amino-4H-chromenes are used as laser dyes, optical brighteners, fluorescence markers, pigments, cosmetics, and potent biodegradable agrochemicals for decades [16–18]. In addition, 2-amino-4H-chromene with cyano- functionality has been also applied in the treatment of rheumatoid, psoriasis, and cancer [19, 20]. Due to the diverse biological application of chromenes, variety of methods has been reported in the literature for the synthesis of the skeleton using different homogeneous or heteroge- neous catalysts. However, it seems that still environmentally friendly and better processes that can provide easy and efficient access to 2-amino-4H-chromene derivatives are sought after [21–24]. Recently, Choudhury et al. reported the multi-compo- nent reaction of malononitrile and aldehydes with various nucleophiles such as 2-hydroxynaphthoquinone in the & Nader Ghaffari Khaligh ngkhaligh@gmail.com; ngkhaligh@um.edu.my 1 Nanotechnology and Catalysis Research Centre, NANOCAT, University of Malaya, Kuala Lumpur, Malaysia 2 Research House of Professor Reza, Education Guilan, District 1, Rasht 41569-17139, Iran 123 Monatsh Chem (2018) 149:33–38 https://doi.org/10.1007/s00706-017-2059-9