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3-Azido-2-azetidinones

Various nucleophilic attacks at C(3) and C(4) of -lactams have been employed to introduce desired functionalities. Nucleophilic displacement of a halogen at C(3) by nucleophiles, for example, potassium phthalimide, has been performed (93JCS(Pl)2357). The a-azidation of l-hydroxy-2-azetidi-nones, for example (37), with arenesulfonyl azides in the presence of triethylamine affords 3-azido-2-azetidinones (38) via Otosylation and SN2 -type of displacement of the tosyloxy group (92JA2741, 93JA548, 93BMC2429). [Pg.487]

Mercaptoazetidinones may be prepared from penicillins or from the reaction of azidoacetyl chloride with thioimidates. 3-Azido-2-azetidinones are converted into 3-acylamino-2-azetidinone via the intermediacy of a phos-phinimine by reaction with acid chlorides. Good yields of a-methylene-/8-lactams are obtained by the insertion of carbon monoxide into various 2-bromo-3-aminopropene derivatives " in the presence of a palladium catalyst (Scheme 123). Further reactions lead to substituted derivatives. [Pg.327]

Azetidine 2-Azetidinecarboxylicacid 2-Azetidinone Azidobenzene 1-Azido-4-chlorobenzene 2-Azidoethanol... [Pg.153]

Nitrogen is introduced into the 3-position of the azetidinone ring as an azido group by reaction of TBS-protected 43 with 2,4,6-triisopropylbenzenesulfonyl azide. The reaction is stereospecific, yielding the desired trans 3S,4R relationship. [Pg.175]

Thallous ethoxide added in one portion at room temp, to a stirred soln. of 3-azido-4-phenyl-2-azetidinone in dimethylformamide, then tert-hutyl a-bromo-acetate in dimethylformamide added during 5 min., and stirred 1 hr. at room temp. l-( err-butoxycarbonylmethyl)-3-azido-4-phenyl-2-azetidinone. Y 50%, -Other methods failed. F. e. s. J. N. Wells and O. R. Tarwater, J. Med. Chem. 14, 242 (1971). [Pg.419]


See other pages where 3-Azido-2-azetidinones is mentioned: [Pg.466]    [Pg.144]    [Pg.412]    [Pg.227]    [Pg.59]    [Pg.56]    [Pg.95]    [Pg.539]    [Pg.466]    [Pg.192]    [Pg.59]    [Pg.1352]   
See also in sourсe #XX -- [ Pg.625 ]




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2-Azetidinone

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