Synthesis, characterization and antibacterial activity of some novel spiro[naphtho[1,2-e][1,3]oxazine-3,4'-pyran] derivatives

Document Type : Original Article


1 Chemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt

2 Botany Department, Faculty of Science, Sohag University, 82524Sohag, Egypt



1-(Aryl(phenylamino)methyl)naphthalen-2-ol derivatives 1a-d were obtained by multicomponent condensation of aromatic
aldehydes, 2-naphthol, and aniline in the presence of ceric ammonium nitrate (CAN) catalyst. Reaction of compounds 1a-d
with a-oxoketene dithioacetal afforded the corresponding oxazines 2a-d. Compounds 2a-d were allowed to react with
malononitrile or cyclopentanone under alkaline conditions where the corresponding spiro heterocycles 3a-d and 4a-d were
formed. Reaction of compounds 1a-d with a-cyanoketene dithioacetal afforded naphtho[1,2-e][1,3]oxazin-3(2H)-
ylidene)malononitrile derivatives 5a-d. By the same way, the reaction of compounds 5a-d with acetylacetone or
cyclopentanone gave the corresponding spiro heterocycles 6a-d and 7a-d respectively. All the obtained products were
identified by their elemental and spectral (IR and NMR) analyses. The antimicrobial activity of the newly synthesized spiro
heterocyclic compounds were tested against the following microorganisms: Gram-positive bacteria [aureus (ATCC 25923)
and S. pyogenes (ATCC 19615)] and Gram-negative bacteria [P. phaseolicola (GSPB 2828) and P. fluorescens (S 97)].