4,5-bis(dimethylamino)quinolines: Proton sponge versus azine behavior

Organic Letters

Volumn 14, Issue 16, 2012, Pages 4134-4137

  Dyablo, Olga V ^a   Shmoilova, Elena A ^a   Pozharskii, Alexander F ^a   Ozeryanskii, Valery A ^a   Burov, Oleg N ^a   Starikova, Zoya A ^b  

^a SOUTHERN FEDERAL UNIVERSITY   (Russian Federation)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84865246483     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301777s     Document Type: Article

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14. The high total yields of 5, 6 and 10, 11 testify that no alkylation at the ring heteroatom seems to occur under these conditions. Obviously, such low nucleophilicity of the quinoline nitrogen atom in these compounds results from its strong shielding by 2- and 8-substituents (see, for example, Pozharskii, A. F. Theoretical bases of heterocyclic chemistry; Khimia: Moscow, 1985; p 135).
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