Abstract
An efficient, straight-forward and eco-friendly synthetic strategy for the assembly of novel bisoxazolones via a four-component, sequential reaction of dialdehydes, glycine, benzoyl chloride and ac ...
Highlights
Arylidene azlactones (4-arylidene-2-phenyl-5(4H)oxazolones) have attracted much interest with respect to their broad range of chemotherapeutic activities.[1,2,3] They are convenient, significant intermediates and building blocks for the assembly of a variety of biologically-active compounds comprising peptides[4,5,6,7] and amino acids.[8,9] these compounds are valuable precursors for the design of photosensitive and biosensors devices for proteins.[10]
As part of our efforts to prepare bis-heterocyclic systems using environmentally-benign conditions,[30,31,32,33,34] we describe, efficient protocols for the preparation of bis-oxazolones and bis-imidazoles driven by ultrasonic irradiation
As a continuation of our work towards developing novel protocols for the synthesis of oxazolones[18] and bisheterocycles from dialdehydes,[30,34] we have progressed with respect to the design and preparation of the bisoxazolones (2a-f)
Summary
Arylidene azlactones (4-arylidene-2-phenyl-5(4H)oxazolones) have attracted much interest with respect to their broad range of chemotherapeutic activities.[1,2,3] They are convenient, significant intermediates and building blocks for the assembly of a variety of biologically-active compounds comprising peptides[4,5,6,7] and amino acids.[8,9] these compounds are valuable precursors for the design of photosensitive and biosensors devices for proteins.[10] The best known strategy for the preparation of oxazolones is generally regarded to be the Erlenmeyer reaction, which involves the reaction of N-benzoylglycine (hippuric acid) with aldehydes in the presence of a basic catalyst (NaOAc) and dehydrating agent (Ac2O).[11] After the Erlenmeyerreaction method, several other catalysts, dehydrating agents and methods have been utilized for condensation of hippuric acid (HA) and several carbonyl compounds.[12,13,14,15] several of these protocols have some disadvantages, including prolonged reaction times, poor yields, use of hazardous chemicals, and often harsh reaction conditions.[16,17] Our group developed a new strategy for the assembly of arylideneoxazolones starting from arylidenemalononitriles using solvent-free conditions.[18] several structural analogs have been prepared, a careful literature survey showed that only one synthetic method has been used for the construction of bisoxazolones.[19] the development of more convenient and ecofriendly strategies for the preparation of oxazolones and bisoxazolones would be advantageous
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