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Digitale Medien

Iodocyclisation of 1,4-Dihydropyridines; Synthesis and Reactivity of 1-Iodoindolo[2,3-a]quinolizidines (1999)

Lavilla, Rodolfo ; Coll, Oscar ; Nicolàs, Marta ; [weitere]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 2997-3003

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Details

ISSN: 1434-193X

Schlagwort(e): Alkaloids ; Cyclizations ; Iodine ; Nitrogen heterocycles ; Oxidations ; Chemistry ; General Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: The addition of iodine (or related species) to β-acyl-N-alkyl-1,4-dihydropyridines 1, which possess an N-substituent with an appropriate nucleophile moiety, leads to the corresponding 3-iododihydropyridinium ions, which undergo an internal nucleophilic attack to give, regio- and stereoselectively, the iodobi(poly)heterocyclic ring systems 2a-f in good yields. Reactivity studies on the iodoindoloquinolizidines 2e,f lead to the pentacyclic cyclopropane systems 4a,b, azides 5 and 6, norderivative 9 and, by a base-induced elimination, dihydropyridine 10, a precursor of the zwitterionic alkaloids flavopereirine and 6,7-dihydroflavopereirine.

Zusätzliches Material: 2 Ill.

Materialart: Digitale Medien

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