111043-42-6Relevant articles and documents
2-ARYLMETHYLAZETIDINE CARBAPENEM DERIVATIVES AND PREPARATION THEREOF
-
Page/Page column 15-16, (2008/06/13)
A 2-arylmethylazetidine carbapenem derivative of formula ( I ) or a pharmaceutically acceptable salt thereof exhibits a wide spectrum of antibacterial activities against Gram-positive and Gram-negative bacteria and excellent antibacterial activities against resistant bacteria such as methicillin-resistant Staphylococcus aureus (MRSA) and quinolone-resistant strains (QRS).
New Synthesis of Propargylic Amines from 2-(Bromomethyl)aziridines. Intermediacy of 3-Bromoazetidinium Salts
D'Hooghe, Matthias,Van Brabandt, Willem,De Kimpe, Norbert
, p. 2703 - 2710 (2007/10/03)
A new, efficient, and straightforward synthesis provides propargylamines in high overall yields (64-77%) by transformation of 1-(arylmethyl)-2-(bromomethyl)aziridines into N,N-di(arylmethyl)N-(2-propynyl)amines via N-(2,3-dibromopropyl)amines and N-(2-bromo-2-propenyl)amines. The conversion of N-(2,3-dibromopropyl)amines into N-(2-bromo-2-propenyl)amines is based on a novel analogue of the Hofmann elimination. A Yamaguchi-Hirao alkylation, a Sonogashira coupling, or a hydroarylation reaction further functionalized these propargylamines toward potentially interesting compounds for medicinal and agrochemical use.
Novel Syntheses of 1,3,3-Trinitroazetidine
Katritzky, Alan R.,Cundy, Darren J.,Chen, Jie
, p. 271 - 276 (2007/10/02)
Alternative methods for the synthesis of 1,3,3-trinitroazetidine (TNAZ) from epichlorohydrin, and benzhydrylamine have been developed.These approaches employ N-sulfonyl-3-(hydroxyimino)azetidines as penultimate intermediates and represent an improvement over previously published methods which require either diazo containing intermediates or involve low yielding procedures.Parallel methods employing N-benzhydryl- and N-benzyl-3-(hydroxyimino)azetidine were also investigated as alternate routes to TNAZ
Preparation of Trimethylsilyl Ethers of 3-Azetidinols . Scope and Limitations
Higgins, Robert H.,Watson, Monique R.,Faircloth, William J.,Eaton, Quentin L.,Jenkins, Harvey
, p. 383 - 387 (2007/10/02)
Preparation of the trimethylsilyl ethers of 1-alkyl-3-azetidinols from-non-hindered primary amines and epichlorhydrin by conversion of the intermediate 1-(alkylamino)-3-chloro-2-propanols to their trimethylsilylethers by either N-(trimethylsilyl)acetamide or by 1-(trimethylsilyl)imidazole followed by ring closure in acetonitrile is described.This sequence of reactions fails for aromatic amines, but appears to be general for all primary aliphatic amines, although the condensation of hindered amines with epichlorhydrin occurs slowly.Several novel azetidinols, in which the N-alkyl substituent insefl contains a second heterocyclic system, are reported.In addition, the pKA's of several m- and p-substituted 1-benzylazetidinols correlates well with the Hammett equation.
Preparation of 3-Azetidinols with Non-Bulky 1-Alkyl Substituents
Higgins, Robert H.,Eaton, Quentin L.,Worth, Leroy,Peterson, Myra V.
, p. 255 - 259 (2007/10/02)
Cyclization of either the tetrahydropyranyl or trimethylsilyl ether of 1-(alkylamino)-3-chloro-2-propanols 1 followed by cleavage of the azetidinyl ether provides a general method for the preparation of 1-alkyl-3-azetidinols.Unhindered amines provide a more facile preparation of derivatives of 1, or its ethers, than do hindered amines, while hindered derivatives of 1 undergo more facile ring closure.
The Effect of the Steric Requirements of Trialkylsilyl Ethers on Ring Closure of 1-(Benzylamino)-3-chloro-2-(trialkylsiloxy)propanes
Higgins, Robert H.
, p. 1489 - 1491 (2007/10/02)
The ring closure of 1-(benzylamino)-3-chloro-2-(trialkylsiloxy)propanes to 1-benzyl-3-(trialkylsiloxy)azetidines was investigated.There appears to be little or no advantage in the use of trialkylsilyl substituents larger than trimethylsilyl.
