An original TiCl4/t-Bu-NH2 mediated hydroamination/annulation domino reaction of delta-keto-acetylenes is described. The synthesis of pyrrolo[1,2-a]indole-2-carbaldehydes, starting from 2-carbonyl-1-propargyl-1H-indoles run under mild reaction conditions. A conceivable mechanism is also discussed. TiCl4 has proved to be an effective multi-activity reagent: catalyst / Lewis acid / water scavenger. Some unpublished 2-carbonyl-1-propargyl-1H-indoles are prepared by means of Suzuki- and Negishi-type reactions.

TiCl4/t-BuNH2-promoted hydroamination/annulation of delta-keto-acetylenes : synthesis of novel pyrrolo[1,2-a]indol-2-carbaldehydes / G. Abbiati, A. Casoni, V. Canevari, D. Nava, E. Rossi. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 8:21(2006 Aug), pp. 4839-4842.

TiCl4/t-BuNH2-promoted hydroamination/annulation of delta-keto-acetylenes : synthesis of novel pyrrolo[1,2-a]indol-2-carbaldehydes

G. Abbiati
Primo
;
A. Casoni
Secondo
;
V. Canevari;D. Nava
Penultimo
;
E. Rossi
Ultimo
2006

Abstract

An original TiCl4/t-Bu-NH2 mediated hydroamination/annulation domino reaction of delta-keto-acetylenes is described. The synthesis of pyrrolo[1,2-a]indole-2-carbaldehydes, starting from 2-carbonyl-1-propargyl-1H-indoles run under mild reaction conditions. A conceivable mechanism is also discussed. TiCl4 has proved to be an effective multi-activity reagent: catalyst / Lewis acid / water scavenger. Some unpublished 2-carbonyl-1-propargyl-1H-indoles are prepared by means of Suzuki- and Negishi-type reactions.
Intramolecular cyclization; indole alkaloids; 1,3-dipolar cycloadditions; titanium tetrachloride; entry; derivatives; chemistry; alkynes; neucleophiles
Settore CHIM/06 - Chimica Organica
ago-2006
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/43057
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