ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis of (Z/E)-1-Aryl-4-arylmethylene-pyrrolidine-2,3,5-triones and Reactions with HeteronucleophilesThe condensation reaction of 2-hydroxy-maleimides 1 prepared in situ from 2-ethoxycarbonyl-3-hydroxy-maleimide 2 or the amide ester 3 with aldehydes afforded in a one-pot procedure the (Z/E)-1-aryl-4-arylmethylene-pyrrolidine-2,3,5-triones 5a-k in good yields.Acid catalyzed treatment of the α,β-unsaturated carbonyl compounds (Z/E)-5a, c, g with bifunctional nucleophiles such as thiourea and phenylthiourea gave the derivatives of 1,3-thiazine-2-ones 8a-d respectively, while (Z/E)-5f and urea produced the pyrimidine-2-ones 9. Under the insemicarbacide led to the formation of the (Z/E)-isomers 10a-f.Triethyl phosphite added in a Michael fashion to yield the novel 3-aryl-2,2,2-triethoxy-Δ4-oxaphospholene-4,5-dicarboxylic imides 11a-c.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19873290413
