6533b7cffe1ef96bd1258c68
RESEARCH PRODUCT
Selective derivatisation of resorcarenes: 1. The regioselective formation of tetra-benzoxazine derivatives
Volker BöhmerErich F. PaulusKarri AirolaChristian SchmidtWalter VogtKari RissanenIris Thondorfsubject
biologyChemistryHydrogen bondOrganic ChemistryCondensationFormaldehydeRegioselectivitybiology.organism_classificationBiochemistryMedicinal chemistrychemistry.chemical_compoundIntramolecular forceDrug DiscoveryStructural isomerTetraOrganic chemistrySingle crystaldescription
Abstract Four 5,6-benzo-1,3-oxazine rings are formed by the condensation of resorcarenes with various aliphatic or aromatic primary amines and formaldehyde. From four possible regioisomers only the C4 symmetrical compound is isolated in yields of up to 90%. Semiempirical calculations confirm its relative stability, which is due to the possible formation of four intramolecular OH…O hydrogen bonds. The regioselectivity of the reaction is further established for two examples by single crystal X-ray analysis. A solvent molecule is included in the extended cavity.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1997-08-01 | Tetrahedron |