Mol Divers DOI 10.1007/s11030-015-9573-7 SHORT COMMUNICATION A one-pot three-component reaction involving 2-aminochromone in aqueous micellar medium: a green synthesis of hexahydrochromeno[2,3- b]quinolinedione Jaydip Ghosh · Pritam Biswas · Michael G. B. Drew · Chandrakanta Bandyopadhyay Received: 2 September 2014 / Accepted: 22 February 2015 © Springer International Publishing Switzerland 2015 Abstract An efficient and green synthesis of hitherto unre- ported 11-(chromen-3-yl)-8,8-dimethyl-8,9-dihydro-6H- chromeno[2,3-b]quinoline-10,12(7H,11H)-dione has been accomplished by a three-component reaction involving 2- aminochromone, chromone-3-carbaldehyde, and 5,5-dimethyl- 1,3-cyclohexanedione (dimedone) in 0.5 M aqueous SDS solution. The mechanism of the reaction has been studied by isolating the reaction intermediate. This methodology fea- tures eco-friendly reaction conditions, a simple working pro- cedure, high atom-economy and high efficiency in product formation. Graphical abstract Keywords 2-Aminochromone · Chromone · Chromone-3- carbaldehyde · Green chemistry · Micelle · Multicomponent reaction · MCRs · Surfactant Electronic supplementary material The online version of this article (doi:10.1007/s11030-015-9573-7) contains supplementary material, which is available to authorized users. J. Ghosh · P. Biswas · C. Bandyopadhyay (B ) Department of Chemistry, R. K. Mission Vivekananda Centenary College, Rahara, Kolkata 700118, West Bengal, India e-mail: kantachandra@rediffmail.com M. G. B. Drew Department of Chemistry, The University of Reading, P. O. Box 224, Whiteknights, Reading RG6 6AD, UK Introduction A multicomponent reaction (MCR) with high atom econ- omy, carried out under green reaction conditions avoiding the use of organic solvents to produce useful molecular scaf- folds in high yield is an attractive synthetic process [1–3]. Synthesis of natural products and biologically active poly- cyclic heterocycles by MCRs is always an organic synthesis challenge [4–7]. In recent years, the use of hazardous sol- vents and toxic chemicals is strongly discouraged and syn- thetic chemists are trying to carry out organic reactions under solvent-free condition or in aqueous medium [8–11]. Despite of the poor water solubility many organic compounds exhibit, many organic reactions have been efficiently carried out in aqueous medium [12]. Factors responsible for organic reac- tions in aqueous medium include the Breslow hydrophobic effect [13], H-bonding, polarity effect and the Marcus trans- phase H-bonding phenomena [14]. Another approach to carry out organic reactions in aqueous medium is by using micelles [15–17]. The ubiquity of the chromone skeleton in natural prod- ucts and in pharmaceutically important compounds [18– 25] demands the synthesis of new chromone-linked and/or chromone-fused polycyclic heterocycles. Chromenoquino- lines are an important class of compounds having various biological activities depending on the nature of the two fused heterocycles. Chromeno[2,3-g]quinoline-3-carboxylates act as anticoccidal drugs [26], naphthopyrano[4,3-b]quinolines have been utilized for developing probes for bioimag- ing [27, 28], 6 H -chromeno[4,3-b]quinolines act as estrogen receptor β-selective ligands [29], chromeno[4,3-b]quinoline derivatives exhibit cytotoxicity [30], tetrahydrochromeno [4,3-b]quinolines exhibit anti proliferative activity against MDA-MB-231 and MCF-7 breast cancer cell lines [31], 5 H - chromeno[3,4- f ]quinolines act as glucocorticoid and selec- 123