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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Published in | Tetrahedron Vol. 53; no. 52; pp. 17691 - 17698 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
29.12.1997
Elsevier |
Subjects | |
Online Access | Get full text |
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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.
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ISSN: | 0040-4020 1464-5416 |
DOI: | 10.1016/S0040-4020(97)10236-8 |