ISSN:
0018-019X
Schlagwort(e):
Chemistry
;
Organic Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
Acid-Catalyzed Reactions of 2-Vinylaniline Derivatives with 1-Benzyl- and 1-Methylpiperidin-4-one: An Elegant Synthesis of New Polycyclic Indole DerivativesThe reaction of 2-vinylaniline derivatives with 1-benzylpiperidin-4-one or 1-methylpiperidin-4-one in toluene at temperatures between 115 and 120° with toluene-4-sulfonic acid as catalyst leads in good yields to a new class of polycyclic indole derivatives (Scheme 1, Table 1). The structure of the new diastereoisomerically pure racemic compounds 1-5 is determined by NMR-spectroscopic methods. A reaction mechanism proceeding via cyclization of enamine 9, leading to a racemic, tricyclic reactive intermediate 10, and subsequent intramolecular 1,5-dipolar cyclization as key steps in proposed for the formation of octahydropyrido[4′,3′:4]cyclobut[1,2-b]indoles 1-5. The scope and limitations of the new method are discussed (see Table 2).
Zusätzliches Material:
2 Tab.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/hlca.19930760407
Permalink