ISSN:
1434-193X
Keywords:
Nitrogen heterocycles
;
Open-chain analogue of Reissert compound
;
Hydrofluoroborate salts
;
α,β-Ethylenic esters
;
1,3-Dipolar cycloaddition
;
Azomethine ylide
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
-The reaction of the hydrofluoroborate salt of an open-chain analogue of a Reissert compound with some α,β-ethylenic esters does not give a [4 + 2] cycloadduct, as previously described in the case of ethyl acrylate. The reaction starts with a 1,3-dipolar cycloaddition of a münchnone imine 5c, d. The [3 + 2] cycloadducts 13 evolve via a rearrangement-condensation sequence to give a substituted 2-pyridone derivative 18 or 19. The proposed mechanism has been verified by the isolation and structural X-ray analysis of some compounds of the reaction sequence.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
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