General pathway for a convenient one-pot synthesis of trifluoromethyl- containing 2-amino-7-alkyl(aryl/heteroaryl)- 1,8-naphthyridines and fused cycloalkane analogues
Molecules, ISSN: 1420-3049, Vol: 16, Issue: 4, Page: 2817-2832
2011
- 14Citations
- 24Captures
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Article Description
A convenient and general method for the synthesis in 26-73% yields of a new series of 7-alkyl(aryl/heteroaryl)-2-amino-5-trifluoromethyl-1,8-naphthyridines from direct cyclocondensation reactions of 4-alkoxy-1,1,1-trifluoroalk-3-en-2- ones [CFC(O)CH=C(R)OR, where R = H, Me, Ph, 4-MePh, 4-OMePh, 4-FPh, 4-BrPh, 4-NOPh, 2-furyl, 2-thienyl and R = Me, Et] with 2,6-diaminopyridine (2,6-DAP), under mild conditions, is described. Another synthetic route also allowed the synthesis of 2-amino-5- trifluoromethyl-cycloalka[b][1,8]naphthyridines in 33-36% yields, from direct or indirect cyclo-condensation reactions of five-, six- and seven-membered 2-trifluoroacetyl-1-methoxy-cycloalkenes with 2,6-DAP. © 2011 by the authors.
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