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The Proton Sponge Effect: Substitution of Quino[7,8‐ h ]quinoline and the First Structurally Characterised Derivatives

2012; Wiley; Volume: 2012; Issue: 35 Linguagem: Inglês

10.1002/ejoc.201201131

1434-193X

Karl J. Shaffer, D.C. Parr, Marco Wenzel, Gareth J. Rowlands, Paul G. Plieger,

Supramolecular Chemistry and Complexes

Abstract A new route to unsymmetrical derivatives of quino[7,8‐ h ]quinoline was developed. Substitutions at the 2,11‐, 4,9‐ and 6,7‐positions of quino[7,8‐ h ]quinoline were also successfully performed. X‐ray crystal structure determinations of the resulting products revealed the propensity for derivatives of this molecule to exist in either stabilised keto or imino forms as a result of the formation of a strong intramolecular N–H ··· N hydrogen bond.