Synthesis of azetidin-3-ones. Structure of N-tosyl-2-ethylazetidin-3-one

A one-step synthesis of azetidin-3-ones by intramolecular cyclization of 1-diazo-3-arenesulfamoylalkan-2-ones was developed. The yield of cyclic product increases to 70% in the presence of an alkyl or benzyl substituent in the hydrocarbon chain of the diazoketone. The structure of N-tosyl-2-ethylaze...

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Veröffentlicht in:	Chem. Heterocycl. Compd. (Engl. Transl.); (United States) 1987-04, Vol.23 (4), p.390-395
Hauptverfasser:	Aliev, Z. G., Atovmyan, L. O., Sipyagin, A. M., Kartsev, V. G., Dobrokhotova, O. V.
Format:	Artikel
Sprache:	eng
Schlagworte:	400201 - Chemical & Physicochemical Properties 640302 - Atomic, Molecular & Chemical Physics- Atomic & Molecular Properties & Theory ATOMIC AND MOLECULAR PHYSICS CHEMICAL REACTION YIELD CHEMICAL REACTIONS CHEMICAL SHIFT CHLORINATED ALIPHATIC HYDROCARBONS CHLOROFORM COHERENT SCATTERING CONFIGURATION INTERACTION COUPLING COUPLING CONSTANTS DEHYDROCYCLIZATION DEUTERIUM COMPOUNDS DIFFRACTION ENERGY LEVELS EXCITED STATES HALOGENATED ALIPHATIC HYDROCARBONS HETEROCYCLIC COMPOUNDS HYDROGEN COMPOUNDS INFRARED SPECTRA INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY INTERMEDIATE COUPLING ISOMERIZATION ISOTOPE EFFECTS J-J COUPLING KETONES NMR SPECTRA ORGANIC CHLORINE COMPOUNDS ORGANIC COMPOUNDS ORGANIC HALOGEN COMPOUNDS ORGANIC NITROGEN COMPOUNDS ORGANIC SULFUR COMPOUNDS SCATTERING SPECTRA SYNTHESIS ULTRAVIOLET SPECTRA VIBRATIONAL STATES X-RAY DIFFRACTION YIELDS
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Beschreibung
Zusammenfassung:	A one-step synthesis of azetidin-3-ones by intramolecular cyclization of 1-diazo-3-arenesulfamoylalkan-2-ones was developed. The yield of cyclic product increases to 70% in the presence of an alkyl or benzyl substituent in the hydrocarbon chain of the diazoketone. The structure of N-tosyl-2-ethylazetidin-3-one was studied by x-ray diffraction analysis and it was shown that the four-membered ring has 15/sup 0/ inflection. IR spectra were recorded with a Specord 75 IR instrument in mineral oil. PMR spectra were recorded with Bruker WH-360 (360 MHz) and Jeol HL-60 (60 MHz) instruments in CDCl/sub 3/ solution, with TMS internal standard. UV spectra were obtained with a Specord UV-VIS instrument in methanol.
ISSN:	0009-3122 1573-8353
DOI:	10.1007/BF00546731