4-Iminocyclobutenones: Synthesis and Building-Blocks of Aminohydroquinones and Annulated Quinolines

Abstract

Two methods are presented for the synthesis of the title compounds starting from cyclobutenediones: an alkoxide substitution approach and a Staudinger reaction. Unsaturated lithiumorganyls may be added to the remaining carbonyl group and on heating lead to ring enlargement in a cascading process. 4-Alkenyl or 4-aryl derivatives yield aminophenols or -naphthols; 4-alkynyl compounds give cyclopenta-annulated quinolines.

Key words

alkenes - Schiff bases - electrocyclic reactions - ring expansion - ring opening

References

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21

Unit cell parameters: a = 10.4030(13) Å, b = 13.3488(11) Å, c = 25.005(2) Å, α = 84.276(7)˚, β = 87.124(9)˚, γ = 70.792(9)˚, V = 3262.2(6) Å^³, Z = 6; triclinic, space group P1, R = 0.0452, R _w = 0.0761. CCDC 758016 contains the supplementary cyrstallographic data for this compound. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

22

Unit cell parameters: a = 9.4990(10) Å, b = 17.7990(10) Å, c = 14.7910(10) Å, α = β = γ = 90˚, V = 2500.8(3) Å^³, Z = 4; orthorhombic, space group Pna2(1), R = 0.0542, R _w = 0.1274. CCDC 75 80 17. To obtain the data, see ref. 21.