Aziridinations compounds

Similar to the fullerene modifications using either glycine/formaldehyde derivatives or oxazolidinone compounds, Maggini and Scorrano (1993) found that aziridines could yield similar pyrrolidine derivatives. Heating aziridine compounds in toluene was found to result in ring... 

The residue which was obtained after the removal of the aziridine compound by distillation shows a strong IR absorption peak at l670cm-l which is assigned to v(C=0). Since the aziridine could not be completely removed from the residue because of its close boiling point to the residue, the structure of the residue compound has not been determined in this step. 

Mechanism [ill] represents crosslinking due to aziridine ring formation. This mechanism is supported by the decrease of ethylenic double bond of 1,2-polybutadiene and the fact that a large amount of aziridine compound is formed in the reaction of phenyl-nitrene with unsaturated olefine monomers, although the direct observation of it in 1,2-polybutadiene film matrix has not been accomplished in the present study. 

Another alkylating drug in clinical use is mitomycin C. As a natural product isolated from Stremtomyces lavendulae, mytomycin C is an aziridine compound, which is closely related to nitrogen mustards. This compound is best known to the DNA repair field as a DNA interstrand crosslinking agent. Mytomycin C has been used to treat breast cancer and cancers of the gastrointestinal tract. 

While many of the remaining steps to convert 320 to FR900482 are simple functional group transformations, it is worthwhile to look at some of these steps as examples of reactions that can be undertaken in the presence of an aziridine. Compound 320 is converted to 321 through a series of deprotection, oxidation, and N-protection. The enolate of 321 is treated with formaldehyde to generate 322 as a seperable 1 1 mixture of diastereomers. The unwanted diastereomer could be converted to a 70 30 mixture of diastereomers by treatment with DBU in toluene. The hydroxyl of 322 was protected and then the compound was oxidized with dimethyldioxirane (DMDO) to provide intermediate W-oxide 323. Loss of anisaldehyde followed by intramolecular cyclization provided the tetracyclic 324 (Scheme 63). This compound was then converted to FR900482. 

Cp2TiMe2 is a suitable reagent for the methylenation of heteroatom-substituted carbonyl compounds in the reactions with a- and /3-lactams (Scheme 522). It reacts with l-aryl-2-azetidinones with the formation of methylene azetidine compounds. Analogous reactions with aziridinines afford methylene aziridine compounds.1339... 

Treatment of cotarnine, hydrastinine, or other 3,4-dihydroisoquinoline compounds with diazomethane led to the addition of a CH2 group to the double bond and thus to formation of the aziridine compound. 3,4-Dihy-dropapaveraldine methiodide with diazomethane gave the benzazepine... 

Aziridine compounds having two or more pendant aziridine rings have been described as alternative cross-linkers for EPI adhesives, offering approximately the same reactivity as isocyanates [4]. To the best of oixr knowledge these compounds are not frequently used. 

A. N-Substituted Aziridine and Dibasic Acid Anhydride. Just as alkylene oxide under appropriate condition can altematingly copolymerize with acid anhydride to yield polyester, aziridine compounds can also copolymerize similarly with acid anhydride to form polyamidoester. 

Aziridine compounds Polymers with carboxyl base... 

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