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• 108-98-5 thiophenol 
• 100-46-9 benzylamine 
• 72551-10-1 N-(2-bromoallyl)benzylamine 
• 87672-77-3 N-benzyl-β,β'-dibromoisobutyramide 
• 4383-22-6 Allylbenzylamine 
• 691409-20-8 benzaldehyde O-(N-benzyl-prop-2-enylaminooxalyl)oxime 
• 72551-11-2 N-benzyl-3-methyleneazetidin-2-one 
• 4010-62-2 methyl 3-(benzylamino)-2-methylpropanoate 
• 66839-25-6 2-methyl-3-benzylaminopropanoic acid 

Relevant academic research and scientific papers

A CONVENIENT METHOD FOR THE CONSTRUCTION OF β-LACTAM COMPOUNDS FROM β-AMINO ACIDS USING 2-CHLORO-1-METHYLPYRIDINIUM IODIDE AS CONDENSING REAGENT

Various β-lactams are prepared from the corresponding β-amino acids under mild reaction conditions in high yields by employing 2-chloro-1-methylpyridinium iodide as a condensing reagent.

Use of 2,2′-dibenzothiazolyl disulfide-triphenylphosphine and Lawesson's Reagent in the cyclization of β-amino acids

The disulfide reagents 2,2′-dithiobisbenzothiazole (MBTS) and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (Lawesson's Reagent, LR) mediate the cyclization of β-amino acids with remarkable product yields. Compared to other cyclodehydrating agents, these have been found to be superior in terms of their cost, making them industrially viable. The advantageous properties of MBTS and LR make them useful and unique additions to the arsenal of cyclodehydrating agents.

Generation and cyclization of unsaturated carbamoyl radicals derived from S-4-pentynyl carbamothioates under tin-free conditions

The radical reaction of benzenethiol with S-4-pentynyl carbamothioates provides a valuable protocol for the tin-free generation of carbamoyl radicals, which arise from intramolecular substitution at sulfur by the initial sulfanylvinyl radicals. This procedure can be usefully employed to achieve N-benzylcarbamoyl radical 5-exo and 4-exo cyclizations leading, respectively, to pyrrolidinones and azetidinones, although, for the latter, it seems of lesser utility. Novel evidence is presented that. N-tosyl-substituted carbamoyl radicals display a peculiar tendency to yield the corresponding isocyanate by β-elimination of the tosyl radical.

(Chloromethylene)dimethylammonium chloride: A highly efficient reagent for the synthesis of β-lactams from β-amino acids

(Chloromethylene)dimethylammonium chloride 1, is a unique reagent that conveniently and efficiently mediates the amide bond formation in β-lactams via cyclodehydration of β-amino acids leading to β-lactam formation. The process involves the formation of a highly reactive activated ester of a β-amino acid which gets cyclised to the corresponding β-lactam in excellent yield. The reaction proceeds smoothly and cleanly as the by-products formed are the water soluble-dimethyl formamide and triethylamine hydrochloride.

Preparation of β- and γ-lactams from carbamoyl radicals derived from oxime oxalate amides

A general synthetic route to oxime oxalate amides was developed and applied to the preparation of molecules incorporating N-benzyl-N-alkenyl amides linked with acetone oxime or benzaldoxime units. In addition, 2-substituted-thiazolidine-4-carboxylic acid methyl ester amides of oxalyl benzaldoxime were also prepared. It was shown by EPR spectroscopy that the oxalyl benzaldoxime amides dissociated to produce benziminyl and carbamoyl (aminoacyl) radicals when photolysed with 4-methoxyacetophenone as a photosensitizer. Carbamoyl radicals derived from N-alk-3-enyl oxime oxalate amides underwent ring closure to afford pyrrolidin-2-ones. The analogous N-alk-2-enyl precursors afforded azetidin-2-ones. Reactions of the cyclohexenyl and cinnamyl oxime oxalate amides afforded a bicyclic β-lactam and a 3-benzyl-substituted β-lactam respectively. Interestingly, both products were isolated as hydroxylated compounds. A thiazolidine-derived oxime oxalate amide containing an isobutenyl side chain also dissociated with production of the corresponding thiazolidinyl-carbamoyl radical, as shown by EPR spectroscopy. GC-MS evidence indicated that this radical cyclised to afford some of the corresponding penicillin derivative.

Synthesis of monocyclic β-lactams via cyclodehydration of β-amino acids using POCl3

β-Lactams 2 have been synthesized through a convenient use of POCl3 via cyclodehydration of β-amino acids 1.

Preparation of oxime oxalate amides and their use in free-radical mediated syntheses of lactams

Photosensitised decomposition of oxime oxalate amides is a useful new route to carbamoyl radicals that may cyclise to afford β- or γ-lactams.

A facile synthesis of β-lactams by the cyclization of β-amino acids exploiting 3,3′-(phenylphosphoryl)-bis(1,3-thiazolidine-2-thione)

3,3′-(Phenylphosphoryl)-bis(1,3-thiazolidine-2-thione) (5), obtained from phenylphosphonic dichloride (7) and sodium salt of 1,3-thiazolidine-2-thione (6), proved to be useful for intramolecular dehydration of various β-amino acids to give the correspondi

NEW CONDENSING REAGENTS: THIOPHOSPHORUS COMPOUNDS ACTIVATED BY 2-OXAZOLONE AND 2-BENZOXAZOLINONE HETEROCYCLES

The thiophosphorus compounds (3-6) activated by 2-oxazolone and 2-benzoxazolinone heterocycles, which have the advantages of high solubility in organic solvents and good preservability, serve well as versatile condensing reagents for one-step formation of amides including β-lactams, esters and thioesters from carboxylic acids.