Selective derivatisations of resorcarenes - 2. Multiple regioselective ring closure reactions

The condensation of the C-pentyl resorcarene 1 with long chain aliphatic diamines 3a-d and excess formaldehyde leads under high dilution conditions to tetrabenzoxazine derivatives 4a-d in which pairs of adjacent oxazine rings are connected by an aliphatic chain. Six new rings are formed per resorcar...

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Bibliographic Details
Published inTetrahedron Vol. 53; no. 52; pp. 17691 - 17698
Main Authors Schmidt, C., Airola, K., Böhmer, V., Vogt, W., Rissanen, K.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 29.12.1997
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CAVITANDS
MACROCYCLES
RESORCINOL
COMPLEXES
ENERGIES
DERIVATIVES
CALIX RESORCINARENE
CALIXARENES
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Summary:The condensation of the C-pentyl resorcarene 1 with long chain aliphatic diamines 3a-d and excess formaldehyde leads under high dilution conditions to tetrabenzoxazine derivatives 4a-d in which pairs of adjacent oxazine rings are connected by an aliphatic chain. Six new rings are formed per resorcarene molecule during this reaction in a regioselective way. For one example ( 4a) the chiral cleft-like structure with C 2 symmetry was proved by single crystal X-ray analysis. Hydrolysis of the oxazine rings gives the secondary amine derivatives 5a,b with C 2v symmetry in high yield. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(97)10236-8