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Issue 38, 2013
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Synthesis of 3-tetrazolylmethyl-azepino[4,5-b]indol-4-ones in two reaction steps: (Ugi-azide/N-acylation/SN2)/free radical cyclization and docking studies to a 5-Ht6 model

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Abstract

A series of nine novel 3-tetrazolylmethyl-azepino[4,5-b]indol-4-ones were prepared in moderate to good overall yields in only two reaction steps. The first step consisted of a one-pot sequential process of an Ugi-azide multicomponent reaction, N-acylation and SN2 to give the xanthates. The second step was an intramolecular cyclization under free radical conditions. Also, their binding modes have been modelled using docking techniques.

Graphical abstract: Synthesis of 3-tetrazolylmethyl-azepino[4,5-b]indol-4-ones in two reaction steps: (Ugi-azide/N-acylation/SN2)/free radical cyclization and docking studies to a 5-Ht6 model

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Publication details

The article was received on 01 Jul 2013, accepted on 31 Jul 2013 and first published on 31 Jul 2013


Article type: Communication
DOI: 10.1039/C3OB41349G
Citation: Org. Biomol. Chem., 2013,11, 6470-6476
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    Synthesis of 3-tetrazolylmethyl-azepino[4,5-b]indol-4-ones in two reaction steps: (Ugi-azide/N-acylation/SN2)/free radical cyclization and docking studies to a 5-Ht6 model

    R. E. Gordillo-Cruz, A. Rentería-Gómez, A. Islas-Jácome, C. J. Cortes-García, E. Díaz-Cervantes, J. Robles and R. Gámez-Montaño, Org. Biomol. Chem., 2013, 11, 6470
    DOI: 10.1039/C3OB41349G

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