172093-51-5Relevant articles and documents
On the Reaction of Thienonaphthyridine 5-Oxides and 9-Oxides with Thionyl Chloride and Thionyl Bromide. Some Selective Nucleophilic Reactions
Malm, Johan,Hoernfeldt, Anna-Britta,Gronowitz, Salo
, p. 744 - 750 (2007/10/02)
Thienonaphthyridine 5-oxide (1), 1-bromothienonaphthyridine 5-oxide (4), thienonaphthyridine 5-oxide (6) and thienonaphthyridine 5-oxide (9) all gave the 4-chloro isomers with loss of the N-oxide group in the reaction with thionyl chloride.The reactions were performed at room temperature and gave mostly high yields.Thienonaphthyridine 9-oxide (15), on the other hand, gave a mixture of the 6-,7- and 8-chloro isomers.Thienonaphthyridine 9-oxide did not react under these conditions.Reaction with thionyl bromide gave no brominated products, instead, thienonaphthyridine (3) was obtained from 1 and 15.Various nucleophilic substitutions of 4-chlorothienonaphthyridine (2) were carried out and gave 4-thioxo-4,5-dihydrothienonaphthyridine (11), 4-(piperidyl)thienonaphthyridine (12), 4-(4-methylpiperazin-1-yl)thienonaphthyridine (13) and 4-dimethylaminothienonaphthyridine (14) in good yields. 8-Thioxodihydrothienonaphthyridine (21) was prepared from 15 via 8-bromothienonaphthyridine (20) and 8-oxodihydrothienonaphthyridine (19).Attempts to prepare 21 directly from 19 were not successful.