ISSN:
0009-2940
Keywords:
Azabutadienes
;
Isoxazoles
;
Tetrahydropyridines
;
Diels-Alder reactions
;
Sequential transformations
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Condensation of aldehydes 1a-e with 5-amino-3-methylisoxazole (4) gives the corresponding imines 5a-e with a 2-aza-1,3-butadiene moiety, which cyclize selctively, e.g. 5a to form the trans-fused tetrahydropyridine 7a and 5c to yield the cis-fused cycloadduct 8c. The astounding difference in the selectivity of these reactions is explained by electronic effects and suggests a change in the dominating interactions of the orbitals in the transition structure. The structure of 7a is elucidated by an X-ray analysis.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19921251014
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