A Novel Ring Enlargement of 2H-Azirine-3-methyl(phenyl)amines via Amidinium-Intermediates: A New Synthetic Approach to 2,3-Dihydro-1,3,3-trimethylindol-2-one
- Mekhael, Maged K.G 1Organisch-chemisches Institut der Universität Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland / Mubarak City for Scientific Research and Technology Applications (MCSRTA), Alexandria, Egypt
- Smith, Richard J. 2Organisch-chemisches Institut der Universität Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland
- Bienz, Stefan 2Organisch-chemisches Institut der Universität Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland
- Linden, Anthony 2Organisch-chemisches Institut der Universität Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland
- Heimgartner, Heinz 2Organisch-chemisches Institut der Universität Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland
Published in:
- Zeitschrift für Naturforschung B. - Walter de Gruyter GmbH. - 2002, vol. 57, no. 4, p. 444-452
English
2,2,N-Trimethyl-N-phenyl-2H-azirin-3-amine (1a) was prepared by successive treatment of 2,N-dimethyl-N-phenylpropanamide (18) with phosgene, triethylamine, and sodium azide. Reaction of 1a in THF solution with boron trifluoride gave 2-amino-1,3,3-trimethyl-3H-indolium tetrafluoroborate (19) in high yield.T he latter reacted with acetic anhydride in pyridine to give a mixture of N-(2,3-dihydro-1,3,3-trimethylindol-2-yliden)acetamide (22) and 2,3-dihydro- 1,3,3-trimethylindol-2-one (21).On hydrolysis with aqueous HCl, 22 was converted to 21.T he molecular structures of 19 and 22 were established by X-ray crystal structure determination.
- Language
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- English
- Open access status
- green
- Identifiers
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- DOI 10.1515/znb-2002-0410
- ISSN 1865-7117
- Persistent URL
- https://folia.unifr.ch/global/documents/193184
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