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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 |
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| Authors: | Péter Csomós Lajos Fodor Gábor Bernáth Pál Sohár |
| Institution: | a Institute of Pharmaceutical Chemistry, University of Szeged, and Organic Catalysis and Stereochemistry Research Group of the Hungarian Academy of Sciences, H-6701, PO Box 427, Hungary b Central Laboratory, County Hospital, H-5701 Gyula, PO Box 46, Hungary c Institute of Chemistry, Eötvös Loránd University, and Protein Modelling Research Group, Hungarian Academy of Sciences and Eötvös Loránd University, PO Box 32, H-1518 Budapest, Hungary |
| Abstract: | An efficient and selective non-acidic protocol has been developed for the synthesis of derivatives of a new ring system: 4-aryl-1,3-thiazino5,6-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. |
| Keywords: | Amidomethylation 4-Thiaharmalan Thiazino[5 6-b]indole Bischler-Napieralski reaction |
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