A new solvent cum reagent system comprising of water extract of banana ash and dimethylsulfoxide (WEB‐DMSO) has been engaged for the first time to promote the aldol type condensation reaction of aldehydes with ethyl diazoacetate. The condensation reaction has smoothly undergone producing a range of α‐diazo‐β‐hydroxy esters in good to excellent yields. The solvent system has been reused up to five times without loss of its catalytic activity. Further, two one‐pot sequential reactions have been developed in the same reaction medium. First, the methodology has been extended to synthesize β‐keto esters through Pd catalyzed 1,2‐hydrogen migration. Secondly, β‐keto esters have been converted to imidazo[1,2‐a]pyridine‐3‐carboxylates by using N‐bromosuccinimide and 2‐aminopyridines in a one‐pot fashion.
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