Aromatic nucleophilic N-N, N-S and N-O exchange reactions: Efficient synthesis of 5,7-bis (trifluoroacetyl)-8-quinolylamines, sulfides and ethers

Authors
Okada, E Tsukushi, N Shimomura, N
Citation
E. Okada et al., Aromatic nucleophilic N-N, N-S and N-O exchange reactions: Efficient synthesis of 5,7-bis (trifluoroacetyl)-8-quinolylamines, sulfides and ethers, SYNTHESIS-S, (2), 2000, pp. 237-242
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
2
Year of publication
2000
Pages
237 - 242
Database
ISI
SICI code
0039-7881(200002):2<237:ANNNAN>2.0.ZU;2-#
Abstract
Various 5,7-bis(trifluoroacetyl)-8-quinolylamines sulfides and ethers were synthesized in excellent yields by aromatic nucleophilic N-N, N-S and N-O e xchange reactions of N,N-dimethyl-5,7-bis(trifluoroacetyl)-8-quinolylamine with amines, thiols and alcohols. Base-catalyzed cyclization of the resulti ng benzyl 8-quinolyl sulfide and subsequent dehydration gave fluorine-conta ining thieno[3,2-h]quinolines in high yields.