A novel InCl3-mediated one-pot reaction leading to 1-aminocarbazoles is reported. Starting from easily available 2-acetyl-1H-indole, the reaction involves the alkylation of C-3 with a prop-2-yn-1-ol followed by a domino aminobenzannulation reaction in the presence of a secondary amine. The indium salt is most likely involved as catalyst in all three steps of the one-pot reaction. Starting from 2-acetyl-1H-indole and a series of prop-2-yn-1-ols and secondary amines a small library of products has been obtained.
InCl3-assisted one-pot synthesis of 1-aminocarbazoles / D. Facoetti, G. Abbiati, M. Dell'Acqua, E. Rossi. - In: TETRAHEDRON. - ISSN 0040-4020. - 67:36(2011 Sep 09), pp. 6833-6837.
InCl3-assisted one-pot synthesis of 1-aminocarbazoles
D. FacoettiPrimo
;G. AbbiatiSecondo
;M. Dell'AcquaPenultimo
;E. RossiUltimo
2011
Abstract
A novel InCl3-mediated one-pot reaction leading to 1-aminocarbazoles is reported. Starting from easily available 2-acetyl-1H-indole, the reaction involves the alkylation of C-3 with a prop-2-yn-1-ol followed by a domino aminobenzannulation reaction in the presence of a secondary amine. The indium salt is most likely involved as catalyst in all three steps of the one-pot reaction. Starting from 2-acetyl-1H-indole and a series of prop-2-yn-1-ols and secondary amines a small library of products has been obtained.
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