Synthesis and antibacterial activity of some novel spiro [3H-indole-3,5 '-[1,3,4]oxadiazolo[3,2-c]thiazole]-2(1H)-ones and [1,3,4]oxadiazino[6,5-b]indoles containing 1,8-naphthyridine moiety
K. Mogilaiah et al., Synthesis and antibacterial activity of some novel spiro [3H-indole-3,5 '-[1,3,4]oxadiazolo[3,2-c]thiazole]-2(1H)-ones and [1,3,4]oxadiazino[6,5-b]indoles containing 1,8-naphthyridine moiety, I J CHEM B, 38(10), 1999, pp. 1203-1207
Citations number
22
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY
Interaction of 2-phenyl-1,8-naphthyridine-3-carboxylic acid hydrazide 1 wit
h different isatins 2 gives the corresponding isatin-beta-(2-prenyl-1,8-nap
hthyridine-3-carbonylhydrazones) 3. Cyclocondensation of 3 with mercaptoace
tic acid in DMF in the presence of anhyd. ZnCl2 affords 3'-(2-phenyl-1,8-na
phthyridine-3-carbonylamino)spiro[3H-inole-3,2'-thiazolidine]-2,4' (1H)-dio
nes 4, which on treatment with cone. H2SO4 undergo cyclodehydration to furn
ish the desired 2'-(2-phenyl-1,8-naphthyridin-3-yl) spiro[3H-indole-3,5'-[1
,3,4]oxadiazolo[3,2-c]thiazole]-2(1H)-ones 5. On the other hand, the hydraz
ones 3 on treatment with cone. H2SO4 leads to-the formation of 2-(2-phenyl-
1,8-naphthyridin-3-yl)-[1,3,4]oxadiazino[6,5-b]indoles 6. The structures of
the compounds 3-6 have been established on the basis of their elemental an
alyses and spectral (IR, H-1 NMR and mass) data. The compounds 5 and 6 have
been screened for their antibacterial activity.