A1 Journal article (refereed)
Selective Derivatization of Resorcarenes 6. Mannich Reaction of Resorcarenes with Amino Alcohols (2000)

Schmidt, C., Straub, T., Falàbu, D., Paulus, E., Wegelius, E., Kolehmainen, E., Böhmer, V., Rissanen, K., & Vogt, W. (2000). Selective Derivatization of Resorcarenes 6. Mannich Reaction of Resorcarenes with Amino Alcohols. European Journal of Organic Chemistry, 2000(23), 3937-3944. https://doi.org/10.1002/1099-0690(200012)2000:23%3C3937::AID-EJOC3937%3E3.0.CO;2-X

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Publication details

All authors or editors: Schmidt, Christian; Straub, Thomas; Falàbu, Dezsö; Paulus, Erich F.; Wegelius, Elina; Kolehmainen, Erkki; Böhmer, Volker; Rissanen, Kari; Vogt, Walter

Journal or series: European Journal of Organic Chemistry

ISSN: 1434-193X

eISSN: 1099-0690

Publication year: 2000

Volume: 2000

Issue number: 23

Pages range: 3937-3944

Publisher: Wiley

Publication country: Germany

Publication language: English

DOI: https://doi.org/10.1002/1099-0690(200012)2000:23%3C3937::AID-EJOC3937%3E3.0.CO;2-X

Publication open access: Not open

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The condensation of resorcarenes 1 with various amino alcohols and an excess of formaldehyde was studied. The tetrabenzoxazines 2a−e were found as the only products in the reaction with 6-aminohexan-1-ol, 4-aminobutan-1-ol, and 2-aminoethanol, while 3-aminopropan-1-ol forms the tetraoxazine 3 as the main product. In the case of aminoethanols substituted at the 2-position with alkyl groups, the tetraoxazolidines 4 are the preferred reaction products, while 1-methyl aminoethanol (1-amino-propan-2-ol) yields predominantly the tetrabenzoxazine 2f. The structures of all these compounds have been confirmed by NMR spectroscopy and additionally by single-crystal X-ray analysis in the case of 2a and 4b. In [D6]DMSO, up to 60% of the corresponding, more polar tetrabenzoxazine structure is detected for compounds 3 and 4, while the equilibrium is shifted to the less polar tetraoxazine or tetraoxazolidine in CDCl3. Low-temperature NMR spectra show a C4-symmetrical conformation for the tetraoxazolidines 4 in CDCl3 owing to intramolecular OH···OH···N hydrogen bonds. For chiral residues, two epimeric conformations can be distinguished, one of which is selectively formed for larger substituents at the 2-position.

Free keywords: Resorcarenes; Mannic reaction; Amino Alcohols; X-Ray Structures; NMR

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Last updated on 2021-01-07 at 18:20