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Paper | Special issue | Vol 37, No. 1, 1994, pp.331-345
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S9
On the Bromination of the Three Isomeric Thieo[c]fused 1,5-Naphthyridines and Their 5-N-Oxides

Johan Malm, Anna-Britta Hörnfeldt, and Salo Gronowitz*

*Organic Chemistry 1 Chemical Center, University of Lund, P. O. Box 124, S-221 00, Lund, Sweden


Thieno[3,4-c]-1,5-naphthyridine (1) and its 5-N-oxide (5) were conveniently brominated at room temperature with tetrabutylammonium perbromide in the presence of a large excess of sodium hydrogen carbonate. Compound (1) gave the 1- and 3-bromo derivatives in a 4:1 ratio, while 5 was regioselectively brominated in the 3-position. Thieno[2,3-c]-1,5-naphthyridine (7), its 5-N-oxide (11) and thieno[3,2-c]-1,5-naphthyridine (14) did not react under these conditions, but gave products in the reaction with bromine in refluxing thionyl chloride. Compound (7) gave the 1-brow derivative as main product and interestingly the 1,7-dibromo derivative as by-product. The reaction of 11 and 14 with bromine in thionyl chloride gave mainly chlorinated products.