184583-35-5

Upstream product

• 160624-81-7 N,N'-di-p-toluenesulfonyl-1,5-diazacyclooctane-3,7-dione anti-dioxime 
• 70-55-3 toluene-4-sulfonamide 
• 130927-34-3 3,7-dimethylene-1,5-dimethylbenzenesulfonyl-1,5-diazacyclooctane 
• 160624-80-6 1,5-ditosyl-1,5-diazocane-3,7-dione 

Relevant academic research and scientific papers

1,5-Diazacyclooctane-3,7-Derivatives as Precursors of the 3,7-Diazabicyclooctane and 3,7,10-Heterocyclicpropellane Ring Systems

A simple synthesis of 3,7-disubstituted-1,5-diazacyclooctanes from p-toluenesulfonamides and 3-chloro-2-chloromethylpropene has been developed.Unusual transannular reactions in these eight-membered ring intermediates provide easy access to novel 3,7-diaza

Facile Preparation of 3, 7-Diazabicyclo[3.3.0]octane and 3, 7, 10-Triheterocyclic [3.3.3]Propellane Ring Systems from 1, 5-Diazacyclooctane 3, 7-Derivatives

The cyclodimerization ofp-toluenesulfonamide and 3-chloro-2-(chloromethyl)-l-propene to prepare W, Ar-bis(p-toluenesulfonyl)-3, 7-bis(methylene)-l, 5-diazacyclooctane (la) and its ozonation to the corresponding 3, 7-dione 2a are reported. Unusual transannular cyclizations initiated by lithium aluminum hydride treatment or bromination of la and oxidative coupling of the dioxime derived from 2a are described. These reactions lead, respectively, to the following derivatives of the littlestudied 3, 7-diazabicyclo[3.3.0]octane ring system: l, 5-dimethyl-3, 7-diazabicyclo[3.3.0]octane (5), Ar/'-bis(p-toluenesulfonyl)-l, 5-bis(bromomethyl)-3, 7-diazabicyclo[3.3.0]octane (8), and N, N'-bis(ptoluenesulfonyl)-l, 5-dinitro-3, 7-diazabicyclo[3.3.0]octane, (12). Acid-catalyzed hydration of la, in contrast, gives the expected 5-methyl-3, 7-diazabicyclo[3.3.1]nonan-l-ol (10). Reaction of the dibromide 8 with the nucleophiles, sodium sulfide, sodium oxide, and sodium p-toluenesulfonamide conveniently delivers the corresponding novel 3, 7, 10-triheterocyclic [3.3.3]propellanes.