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Kamlah, Alexandra and Bracher, Franz ORCID logoORCID: https://orcid.org/0000-0003-0009-8629 (2020): A Novel Approach to Highly Substituted β‐Carbolines via Reductive Ring Transformation of 2‐Acyl‐3‐isoxazolylindoles. In: European Journal of Organic Chemistry, No. 18: pp. 2708-2719 [PDF, 1MB]


We have worked out a new approach to 1,3,4‐trisubstituted β‐carbolines of pharmaceutical interest. As central building blocks we used 2‐acylindoles, which are readily available from indole‐2‐Weinreb amides. Bromination at C‐3, followed by Suzuki–Miyaura cross‐coupling with isoxazole‐4‐boronates gives 2‐acyl‐3‐isoxazolylindoles. Ring closure to the β‐carbolines was accomplished by reductive ring transformation upon catalytic hydrogenation in the presence of Cs2CO3.

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