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

Autor:	Heinz Heimgartner, Stefan Bienz, Anthony Linden, Maged K. G. Mekhael, Richard J. Smith
Přispěvatelé:	University of Zurich, Heimgartner, Heinz
Rok vydání:	2002
Předmět:	10120 Department of Chemistry Azirine Tetrafluoroborate 1600 General Chemistry General Chemistry Medicinal chemistry Acetic anhydride chemistry.chemical_compound chemistry 540 Chemistry Pyridine Phosgene Triethylamine Acetamide Boron trifluoride
Zdroj:	ResearcherID
ISSN:	1865-7117 0932-0776
DOI:	10.1515/znb-2002-0410
Popis:	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.
Databáze:	OpenAIRE
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