An Efficient Synthesis of Isoindolo[2,1-a]quinoline Derivatives via Imino Diels-Alder and Intramolecular Diels-Alder Reactions with Furan

Abstract

The straightforward synthesis of new isoindolo[2,1-a]quinoline derivatives from 2,4-disubstituted 1,2,3,4-tetrahydroquinolines bearing a furan fragment via the intramolecular Diels-Alder reaction is reported. The synthesis of key precursors was realized with excellent levels of diastereoselectivity either by Povarov reaction or by a multicomponent condensation approach.

Key words

Povarov reaction - quinolines - furans - intramolecular Diels-Alder reaction - isoindolo[2,1-a]quinolines

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19

Crystallographic data for 6e: C₂₀H₁₉BrN₂O₃, M = 415.28, crystal dimensions: 0.15 × 0.30 × 0.50 mm, light brown prisms, T = 293 K, space group Pc, monoclinic, a = 15.442 (1), b = 20.563 (4), c = 7.855 (2) Å, α = 90.00(3)°, Z = 2, V = 879.0(3) ų; ρ_calcd = 1.569 g/cm^-3, µ(Mo-Kα) = 2.36 cm^-1. The final R ₁ value are 0.0805 (w R _{2 (}F²) = 0.2061) for 1244 independent reflection with I > 2σI (collected/independent reflections 3917/2230 (R _int = 0.0644)), GOOF = 0.999. Full crystallographic data for structure 6 have been deposited with the Cambridge Crystallographic Data Centre (CCDC) as supplementary publication numbers CCDC 256968. 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].