Synthesis of nitro-functionalized polynitrogen tricycles bearing a central 1,2,3-triazolium ylide

Synlett

Volumn , Issue 8, 2009, Pages 1318-1320

  Nyffenegger, Coralie ^a,b   Pasquinet, Eric ^a   Suzenet, Franck ^b   Poullain, Didier ^a   Guillaumet, Gérald ^b  

^a DIF   (France)

^b UNIVERSITÉ D'ORLÉANS   (France)

Author keywords

Cyclizations; Energetic material; Heterocycles; Nitrene; Nucleophilic aromatic substitution

Indexed keywords

1,2,3 TRIAZOLIUM YLIDE; 3 AZIDO 2 CHLOROPYRAZINE; NITROGEN; PYRAZINE; PYRAZOLE; PYRIDINE; TRIAZOLE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRESS; CYCLIZATION; SYNTHESIS;

EID: 67649407417     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1216737     Document Type: Article

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10. Cyclization Procedure Although no problems were encountered with these compounds, they should be considered as energetic compounds and be manipulated with appropriate safety precautions. A suspension of the bicyclic compounds 6-11 (1 mmol) in dichlorobenzene (unless otherwise stated; 10 mL) was stirred at 165°C for 150 min under an inert atmosphere. The resultant mixture was cooled which led to a substantial amount of tricycle precipitating. The solid product was collected by filtration, and more of the product could be collected after concentration of the filtrate under vacuum using a Kügelrohr apparatus. Compound 3 (thermolysis in decalin as solvent) is described in ref. 3.
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