Acid treatment of indole-2-carboxylic acid b- and g-oxoamides causes Friedel–Crafts intramolecular cyclization to b-carbolinones and dihydro-2H-azepino[3,4-b]indol-1-ones, in contrast to secondary d-,3-, and z-oxoamides, which cyclize to the novel heterocyclic rings pyrrolizino[2,1-b]indole, indolizino[2,1-b]indole, and 9a,11-diaza-indeno[1,2-a]azulene, via an intermediate N-acyliminium ion. Tertiary amides lead only the Friedel–Crafts ring closure, thus allowing the synthesis of larger fused rings.

Intramolecular N-acyliminium ion versus Friedel-Crafts cyclization onto 3-indoles : synthesis of the novel rings pyrrolizino[2,1-b]indole and homologues / R. Cincinelli, S. Dallavalle, L. Merlini, R. Nannei, L. Scaglioni. - In: TETRAHEDRON. - ISSN 0040-4020. - 65:17(2009), pp. 3465-3472.

Intramolecular N-acyliminium ion versus Friedel-Crafts cyclization onto 3-indoles : synthesis of the novel rings pyrrolizino[2,1-b]indole and homologues

R. Cincinelli
Primo
;
S. Dallavalle
Secondo
;
L. Merlini;R. Nannei
Penultimo
;
L. Scaglioni
Ultimo
2009

Abstract

Acid treatment of indole-2-carboxylic acid b- and g-oxoamides causes Friedel–Crafts intramolecular cyclization to b-carbolinones and dihydro-2H-azepino[3,4-b]indol-1-ones, in contrast to secondary d-,3-, and z-oxoamides, which cyclize to the novel heterocyclic rings pyrrolizino[2,1-b]indole, indolizino[2,1-b]indole, and 9a,11-diaza-indeno[1,2-a]azulene, via an intermediate N-acyliminium ion. Tertiary amides lead only the Friedel–Crafts ring closure, thus allowing the synthesis of larger fused rings.
Settore CHIM/06 - Chimica Organica
2009
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/58382
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