ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Reactions of (Z/E)-1-Aryl-4-arylmethylene-pyrrolidine-2,3,5-triones with Methylene Active CompoundsThe cyclization of the α,β-unsaturated carbonyl compounds (Z/E)-1a, b with propanedinitrile led to the corresponding 2-amino-3-cyano-4H-pyrans 2a, b. Stable phosphorus containing compounds 3a-c were prepared by Michael type addition between methoxycarbonylmethylene triphenylphosphorane and (Z/E)-1a, c, d in good yields.From (Z/E)-1a, b and dimedone or 2-hydroxy-maleimide Michael adducts 5a, b, 6a were obtained, which converted into 5c, 6b by alkylation with diazomethane or gave different types of heterocycles (7, 8a, b) depending on the reaction conditions.Cyclocondensation of (Z/E)-1b with cycloalkanones in the presence of ammonium acetate formed 4-aryl-1,4-dihydro-cycloalkeno[b]pyridines 9a-c.Further it was shown that the bicyclic 1,4-dihydro-pyridine derivatives 8b and 10, which easily undergo oxidation with CrO3 or air oxygen, were intermediates in the formation of the heteroaromatic compounds 11, 12.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19873290414
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