Thermolysis of 3-Azido-N-Phenylthieno-[2,3-b]pyridine-2-Carboxamides

Design, Synthesis, and Screening of Pyridothieno[3,2-b]indole and Pyridothieno[3,2-c]cinnoline Derivatives as Potential Biologically Active Molecules

“…Azides 5a-q were obtained following a published method 15,17 consisting of successive diazotation of amines 1а-p,r with NaNO2 in a mixture of…”

“…Yield: 0.75 g (85%); orange solid; mp 322-323⁰C (DMSO). IR: 3599 cm -1 (NH (18), 251 (91), 250 (30), 249 (11), 239 (11), 235 (12), 224 (18), 211 (11), 209 (18), 178 (10), 164 (20), 139 (11), 119 (11), 101 (16), 98 (12), 91 (25), 77 (12), 76 (15), 75 (13), 69 (30), 65 (10), 63 (34), 51 (24), 45 (20), 43 (57), 42 (27), 41 (23). Anal.…”

“…IR: 3416 cm -1 (NH). (19), 401 [M] + (100), 372 (29), 371 (48), 356 (14), 355 (74), 327 (27), 313 (14), 299 (15), 298 (24), 297 (18), 284 (12). Anal.…”

“…proach to construct new thieno[2,3-b]pyridines fused with various nitrogen-containing heterocycles, namely, pyridothienodiazepines, 15] thieno[2,3,4-i,j]-2,7-naphthyridines, 16 and pyrido[3',2':4,5]thieno[3,2-b]indoles. 17 In a previous work, 17 we described only several representatives of the new fused heterocyclic system -pyridothienoindole.…”

“…Various approaches for decomposition of the azides are known: photolysis including decomposition with transition metal photocatalysts, 13 and thermolysis. 13b,14 Earlier, we have exploited the last approach to construct new thieno[2,3-b]pyridines fused with various nitrogen-containing heterocycles, namely, pyridothienodiazepines, 15 thieno[2,3,4i,j]-2,7-naphthyridines 16 and pyrido[3',2':4,5]thieno[3,2b]indoles. 17…”