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ONE-POT THREE-COMPONENT REACTION OF NINHYDRIN, 1,3-DICARBONYL COMPOUNDS, AND PRIMARY AMINES TO AFFORD INDENO[1,2-b]PYRROL-4(1H)-ONES

Zinatossadat Hossaini, Hossein Karami, Maryam Sabbaghan, Faramarz Rostami-Charati
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Abstract


A convenient one-pot three-component synthesis of indeno[1,2-b]pyrrol-4(1H)-ones has been developed. The reaction of ninhydrin, 1,3dicarbonyl compounds, and primary amines in the presence of PPh3 in MeCN at room temperature produces the respective indeno[1,2-b]pyrrol-4(1H)-ones in high yields. The synthesized pyrrole derivatives have been used in the Diels–Alder reaction with dialkyl acetylenedicarboxylates in MeCN under reflux conditions to obtain indeno[1,2-b]pyrano[3,4-d]pyrroles in high yields.

 


Keywords


dialkyl acetylenedicarboxylate; 1,3-dicarbonyl compound; ninhydrin; primary amine; pyrrole; Diels–Alder reaction; three-component reaction

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