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Mol Divers (2009) 13:385387 DOI 10.1007/s11030-009-9122-3
SHORT COMMUNICATION
Organic synthesis in water: a green protocol for the synthesis of 2-(cyclohexylamino)-3- aryl- indeno[1,2-b]furan-4-ones
Majid M. Heravi Bita Baghernejad
Hossein A. Oskooie
Received: 13 September 2008 / Accepted: 28 January 2009 / Published online: 28 February 2009 Springer Science+Business Media B.V. 2009
Abstract Aldehydes, 1,3-indandione and cyclohexylisocyanide undergo smooth coupling-cyclization in water to produce the corresponding 2-(cyclohexylamino)-3-aryl- indeno [1,2-b] furan-4-ones in good yields. Water was used as a solvent to avoid the use of other highly toxic and environmentally unfavorable solvents for this synthesis.
Keywords Cyclohexylisocyanide 1,3-Indandione
One-pot Three-component reaction
Furanone is one of the most important heterocycles with widespread occurrence in nature [1,2]. Possessing a variety of biological activities, they are used as pharmaceutical, avor, insecticidal, and sh antifeedant agents [3,4]. Their important biological activities and usefulness as synthetic intermediates of natural products have prompted efforts for better and more environmentally benign synthetic methodologies.
Indenonesareusedasalcoholicfermentationactivators[5], fungicides [6] and potential estrogen binding receptors [7].
Compounds containing the indeno[2,1-b]furan skeleton have attracted interest in bioorganics, natural products, and medicinal chemistry as they are an important class of hetero-cyclic compounds with pharmaceutical and biological activities such as antimicrobial and antifungal properties [811].
Recently, a great attention has been focused on the use of water as green solvent in organic transformations. Water is a desirable solvent for chemical reactions because it is safe,
M. M. Heravi (B) B. Baghernejad H. A. Oskooie
Department of Chemistry, School of Science, Azzahra University, Vanak, Tehran, Irane-mail: [email protected]
B. Baghernejade-mail: [email protected]
non-toxic, environmentally friendly, readily available, and inexpensive compared to organic solvents [1214]. Since the pioneering studies by Breslow [15,16] on DielsAlder reactions, there has been an increasing recognition that organic reactions can proceed well in aqueous media offering key advantages over organic solvents such as rate enhancement and insolubility of the nal products which facilitates their isolation.
Due to the atom economy, convergent character, and simplicity of one-pot procedures, multi-component condensation reactions (MCRs) have an advantageous position among other reactions. The discovery and development of novel MCRs is receiving growing interest from industrial chemistry research groups and represents a new challenge for organic chemists and to the basic understanding of organic chemistry itself [12]. The isocyanide-based MCRs are especially important in this...