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Synthesis 2011(20): 3307-3317  
DOI: 10.1055/s-0030-1260135
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Subburethinam Ramesh, Rajagopal Nagarajan*
School of Chemistry, University of Hyderabad, Hyderabad 500 046, India
Fax: +91(40)23012460; e-Mail: rnsc@uohyd.ernet.in;
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Publication History

Received 29 April 2011
Publication Date:
15 September 2011 (online)

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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.

Key words

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

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15

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: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk 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.