Access to Chromenopyrrole via Tandem [3 + 2] Cycloaddition and Intramolecular C–O Coupling
Bubul Das, Nikita Chakraborty, Hirendra Nath Dhara, P. Bhattacharyya, Bhisma K. Patel
Abstract
A mild and concise method for the synthesis of chromenopyrrole from 2'-hydroxychalcone is devised. The reaction proceeds via an initial [3 + 2] cycloaddition on the C═C bond of 2'-hydroxychalcone and 1,3-dipolarophile, generated in situ by the reaction of ethyl isocyanoacetate and AgOAc. This is then followed by an intramolecular C-O bond formation with the -OH group and C5-H of the in situ generated pyrrole, leading to chromenopyrroles.
Topics & Concepts
Intramolecular forceCycloadditionTandemChemistryIn situPyrroleStereochemistryMedicinal chemistryCombinatorial chemistryCatalysisOrganic chemistryMaterials scienceComposite materialSynthesis and Characterization of PyrrolesOxidative Organic Chemistry ReactionsFluorine in Organic Chemistry