New versatile route to the synthesis of tetrahydro-beta-carbolines and tetrahydro-pyrano[3,4-b]indoles via an intramolecular Michael addition catalyzed by InBr3 |
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Authors: | Agnusdei Marianna Bandini Marco Melloni Alfonso Umani-Ronchi Achille |
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Institution: | Dipartimento di Chimica G. Ciamician, Via Selmi 2, 40126 Bologna, Italy. |
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Abstract: | A simple multistep synthetic strategy to 4-substituted 1,2,3,4-tetrahydro-beta-carboline and 1,3,4,9-tetrahydro-pyrano3,4-b]indole derivatives starting from commercially available indole 2-carboxylic acid (5) is described. The final intramolecular Michael addition promoted by catalytic amount of InBr(3) (5-10 mol %) provided the expected polycyclic compounds in excellent yields (up to 97%) both in anhydrous organic and aqueous media. |
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