Efficient One-Pot Multicomponent Synthesis of (Carbazolylamino)furan-2(5H)-one and Carbazolyltetrahydropyrimidine Derivatives

Abstract

A simple and efficient approach to the synthesis of (carbazolylamino)furan-2(5H)-one derivatives by the three-component reaction of 3-aminocarbazoles, dialkyl acetylenedicarboxylates and aromatic/heterocyclic aldehydes was developed. Further, we describe an ionic liquid mediated, one-pot three-component strategy to synthesize carbazolyltetrahydropyrimidine derivatives from 3-aminocarbazoles, formaldehyde and dialkyl acetylenedicarboxylates.

multicomponent reactions - furan-2(5H)-ones - tetrahydropyrimidines - heteroarylcarbazoles - ionic liquids

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The crystal data of compounds 4a and 6b have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC 808976 (4a) and 808977 (6b). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: [phone]; E-mail: [e-mail] or via http://www.ccdc.cam.ac.uk/data_request/cif. Compound 4a: C₂₇H₂₃N₃O₆; unit cell parameters: a = 8.5722(18) Å, b = 9.8231(18) Å, c = 15.607(3) Å, α = 73.836(16)˚, β = 74.258(18)˚, γ = 76.080(17)˚, space group P1. Compound 6b: C₃₆H₃₄N₄O₄; unit cell parameters: a = 8.9790(6) Å, b = 12.9073(8) Å, c = 15.8140(10) Å, α = 85.908(5)˚, β = 73.556(6)˚, γ = 76.731(6)˚, space group P1.