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

✍ Scribed by Rodolfo Lavilla; Oscar Coll; Marta Nicolàs; Bilal A. Sufi; Javier Torrents; Joan Bosch

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
362 KB
Volume
1999
Category
Article
ISSN
1434-193X

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✦ Synopsis

The addition of iodine (or related species) to β-acyl-N-alkyl-2a-f in good yields. Reactivity studies on the iodoindoloquinolizidines 2e,f lead to the pentacyclic cyclopropane 1,4-dihydropyridines 1, which possess an N-substituent with an appropriate nucleophile moiety, leads to the systems 4a,b, azides 5 and 6, norderivative 9 and, by a baseinduced elimination, dihydropyridine 10, a precursor of the corresponding 3-iododihydropyridinium ions, which undergo an internal nucleophilic attack to give, regio-and zwitterionic alkaloids flavopereirine and 6,7-dihydroflavopereirine. stereoselectively, the iodobi(poly)heterocyclic ring systems [a] Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, tron-withdrawing group at the β-position), a series of

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