Ring-expansion of an aziridinone to a hexahydrotriazine through the agency of a novel rearrangement

✍ Scribed by Mashitah M Yusoff; Erach R Talaty

• Publisher: Elsevier Science
• Year: 1996
• Tongue: French
• Weight: 196 KB
• Volume: 37
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(96)02039-4

✦ Synopsis

Reaction of 1,3-di-t,'rt-bu~.laziridinonc (la) and similar aziridinones with thiosemicarbazide affords, as one of the products, a compound devoid of sulfur, vie., a substituted Naminoimidazolidinone (3a) by selective cleavage of the acyl-nitrogcn bond. Compound 3a undergoes a novel, acid-catalyzed rearrangement to a 3-imino-hexahydro-1,2,4-tri~in-6-one (7a), which can also be obtained ~' treatment of la with hydrazinc followed by BrCN. involving again selective cleavage of the acyl-nitrogen bond.