ISSN:
1434-193X
Keywords:
Alkaloids
;
Cyclizations
;
Iodine
;
Nitrogen heterocycles
;
Oxidations
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
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