NUCLEOPHILIC SUBSTITUTION OF A 4-DIMETHYLAMINO GROUP IN QUINOLINE PROTON SPONGES. STABILIZATION OF 4-QUINOLONES IN HYDROXY FORM. SYNTHESIS OF A PROTON SPONGE BASED ON 8-HYDROXYQUINOLINE

Authors

  • Ольга В. Дябло Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia
  • Александр Ф. Пожарский Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia

DOI:

https://doi.org/10.1007/5301

Keywords:

dimethylaminoquinolines, hydroxyquinolines, methoxyquinolines, quinolones, hydrogen bonding, nucleophilic substitution, proton sponges, tautomerism.

Abstract

Demethylation of methoxy groups in 6(8)-methoxy-2,4,5-tris(dimethylamino)quinolines with 48% HBr leads to nucleophilic substitution
of the 4-NMe2 group with the formation of quinolones existing in solution and the solid state in the hydroxy form stabilized by intramolecular hydrogen bonding. Unlike HBr, the use of BBr3 in the case of the 8-methoxy derivative leads to the formation of 8-hydroxy-2,4,5-tris(dimethylamino)quinoline, a promising ligand for binding of both protic and Lewis acids.

Author Biographies

Ольга В. Дябло, Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia

Доцент кафедры органической химии Южного федерального университета

Александр Ф. Пожарский, Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia

Профессор кафедры органической химии Южного федерального университета

Published

2019-11-13

Issue

Section

Short Communications