1060654-17-2Relevant academic research and scientific papers
Synthesis of 4-thiaharmalan analogue 4-aryl-1,3-thiazino[5,6-b]indole derivatives by prevention of rearrangements to position two of the indole moiety
Csomós, Péter,Fodor, Lajos,Bernáth, Gábor,Csámpai, Antal,Sohár, Pál
, p. 8646 - 8651 (2008)
An efficient and selective non-acidic protocol has been developed for the synthesis of derivatives of a new ring system: 4-aryl-1,3-thiazino[5,6-b]indole, a 4-thiaharmalan analogue. The convenient amidomethylation of indole-3-thiol (5) afforded 3-benzoylaminomethylthio-1H-indole (7a), with ortho-amidomethylated 2-benzoylamino-methyl-3-benzoylaminomethylthio-1H-indole (8) as side product. Following the Bischler-Napieralski reaction of 7a the rearranged 2-benzoylaminomethylthio-1H-indole 11 could be isolated. In order to prevent such rearrangements the target thiazinoindoles were prepared via 3-thiobenzoylaminomethylthioindole (13) via a modified Bischler-Napieralski reaction.
