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The Proton Sponge Effect: Substitution of Quino[7,8‐ h ]quinoline and the First Structurally Characterised Derivatives
Author(s) -
Shaffer Karl J.,
Parr Daniel C.,
Wenzel Marco,
Rowlands Gareth J.,
Plieger Paul G.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201131
Subject(s) - quinoline , chemistry , intramolecular force , hydrogen bond , molecule , stereochemistry , crystal structure , combinatorial chemistry , medicinal chemistry , organic chemistry
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.