ISSN:
0170-2041
Keywords:
Dehydroalanine esters, N-(arylmethylene)-
;
Tetrahydropyridines
;
3,6-Diazabicyclo[3.2.1]oct-2-enes
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
On the Dimerization Reaction of N-(Arylmethylene)dehydroalanine Methyl EstersN-(Arylmethylene)dehydroalanine esters are highly reactive compounds. They dimerize in a [4 + 2] cycloaddition reaction (Diels-Alder reaction) yielding rac-3,4,5,6-tetrahydropyridine derivatives 2 Which can be isolated under suitable conditions. In solution the dimers 2 tautomerize to give the enamines 3 which subsequently undergo a fast intramolecular cyclization reaction yielding the bicyclic compounds. 4. These 3,6-diazabicyclo[3.2.1]oct-2-ene derivatives 4 are formed diastereoselectively. The structure of 4 was established by X-ray analysis. The bicyclic diaminodicarboxylic esters 4 represent the stable final products of this series of transformations.
Notes:
N-(Arylmethylen)dehydroalaninester sind hochreaktive Verbindungen. Sie dimerisieren unter [4+2]-Cycloaddition (Diels-Alder-Reaktion) zu rac-3,4,5,6-Tetrahydropyridin-Derivaten 2, die unter geeigneten Bedingungen isoliert werden können. In Lösung tautomerisieren die Dimeren 2 zu Enaminen 3, die schnell intramolekular zum Bicyclus 4 reagieren. Diese 3,6-Diazabicyclo-[3.2.1]oct-2-en-Derivate 4 werden diastereoselektiv gebildet. Ihre Struktur wurde durch Röntgenstrukturanalyse geklärt. Die bicyclischen Diaminodicarbonsäureester 4 stellen die stabilen Endprodukte der gesamten Reaktionsfolge dar.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.198919890193
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