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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; Smith, Richard J; Bienz, Stefan; Linden, Anthony; Heimgartner, Heinz (2002). 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. Zeitschrift fuer Naturforschung. Section B: A Journal of Chemical Sciences, 57b:444-452.

Abstract

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.The 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-di- hydro-1,3,3-trimethylindol-2-one (21). On hydrolysis with aqueous HCl, 22 was converted to 21.The molecular structures of 19 and 22 were established by X-ray crystal structure determination.

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.The 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-di- hydro-1,3,3-trimethylindol-2-one (21). On hydrolysis with aqueous HCl, 22 was converted to 21.The molecular structures of 19 and 22 were established by X-ray crystal structure determination.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2002
Deposited On:11 Sep 2013 14:42
Last Modified:05 Apr 2016 16:58
Publisher:Verlag der Zeitschrift fuer Naturforschung
ISSN:1865-7117
Funders:Swiss National Science Foundation, F. Hoffmann-La roche AG, Basel
Official URL:http://www.znaturforsch.com/ab/v57b/s57b0444.pdf
Related URLs:http://www.znaturforsch.com/ab/v57b/c57b.htm
Permanent URL: https://doi.org/10.5167/uzh-80789

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