Three component reaction of indane-1,2,3-trione, tosylmethyl isocyanide and benzoic acid derivatives
Ali Reza Kazemizadeh and Ali Ramazani*
Chemistry Department, Zanjan University, P O Box 45195-313, Zanjan, Iran
E-mail:
[email protected]
Abstract
The Passerini reactions of indane-1,2,3-trione, tosylmethyl isocyanide, and benzoic acid derivatives proceed at room temperature giving sterically congested 2,2-disubstituted indane-1,3- dione derivatives in quantitative yield. The reactions are one-pot, and the products obtained did not require any purification.
Keywords: Passerini reaction, isocyanide, indane-1,2,3-trione
Introduction
Multicomponent reactions (MCRs), reactions involving at least three starting materials in a one- pot reaction, remain the most efficient method of rapidly introducing molecular diversity.1-5 As such, they have found widespread use in organic and diversity-oriented synthesis as they provide access highly functionalized molecules in simple and straightforward one-step transformations.6 Among the known multicomponent reactions to date, the most valuable reactions are those based on isocyanides. Isocyanide-based multicomponent reactions (abbreviated to IMCRs by Ugi and Dömling) by virtue of their synthetic potential, their inherent atom efficiency, convergent nature, ease of implementation, and the generation of molecular diversity, have attracted much attention because of the advantages that they offer to the field of combinatorial chemistry.7 IMCRs are particularly interesting because they are more versatile and diverse than the remaining MCRs. The great potential of isocyanides for the development of multicomponent reactions lies in the diversity of bond forming processes available, their functional group tolerance, and the high levels of chemo-, regio-, and stereoselectivity often observed. The outstanding position of IMCRs can be traced back to the exceptional reactivity of the functional group of the isocyanide. No other functional group reacts with nucleophiles and electrophiles at the same atom, leading to the so-called a-adduct. Other functional groups typically react at different atoms with nucleophiles and electrophiles. Moreover, there is virtually no restriction on the nature of the nucleophiles and electrophiles in IMCRs. Other major primary reaction pathways of isocyanides
