Ring-expansion of an aziridinone to a hexahydrotriazine through the agency of a novel rearrangement
Yusoff, Mohd Mashitah Talaty, Erach R.
Yusoff, Mohd Mashitah
Talaty, Erach R.
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1996-11-25
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Mashitah M Yusoff, Erach R Talaty, Ring-expansion of an aziridinone to a hexahydrotriazine through the agency of a novel rearrangement, Tetrahedron Letters, Volume 37, Issue 48,1996, Pages 8695-8698,ISSN 0040-4039, https://doi.org/10.1016/S0040-4039(96)02039-4.
Abstract
Reaction of 1,3-di-tert-butylaziridinone (1a) and similar aziridinones with thiosemicarbazide affords, as one of the products, a compound devoid of sulfur, viz., a substituted N-aminoimidazolidinone (3a) by selective cleavage of the acyl-nitrogen bond. Compound 3a undergoes a novel, acid-catalyzed rearrangement to a 3-imino-hexahydro-1,2,4-triazin-6-one (7a), which can also be obtained by treatment of 1a with hydrazine followed by BrCN, involving again selective cleavage of the acyl-nitrogen bond.
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Elsevier
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Tetrahedron Letters
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00404039