N-(3,4-dihydro-4-oxoquinazolin-3-yl)pyridmium imides: aziridinating agents for alkenes: measurement of rotational barriers around each N–N bond in an N–N–N system

The synthesis of pyridinium imides (III) by reaction of aminoquinazolinones (I) with the corresponding pyridines is given. These imides, except for the cyano-substituted derivative (IIId), function as aziridinating agents for alkenes (cf. (V)). The rotational barriers around each of the N-N bonds in imide (IIIa) are established based on NMR-measurements. -(ATKINSON, R. S.; BARKER, E.; EDWARDS, P. J.; THOMSON, G. A.; J. Chem. Soc., Chem. Commun. (1995) 7, 727-728; Dep. Chem., Univ., Leicester LE1 7RH, UK; EN)

show abstract

Direct Stereoselective Aziridination of Cyclohexenols with 3‐Amino‐2‐(trifluoromethyl)quinazolin‐4(3H)‐one in the Synthesis of Cyclitol Aziridine Glycosidase Inhibitors

Artola

Wouters

Schröder

et al. 2019

Eur J Org Chem

View full text Add to dashboard Cite

Cyclophellitol aziridine and its configurational and functional isomers are powerful covalent inhibitors of retaining glycosidases, and find application in fundamental studies on glycosidases, amongst others in relation to inherited lysosomal storage disorders caused by glycosidase malfunctioning. Few direct and stereoselective aziridination methodologies are known for the synthesis of cyclophellitol aziridines. Herein, we present our studies on the scope of direct 3‐amino‐2‐(trifluoromethyl)quinazolin‐4(3H)‐one‐mediated aziridination on a variety of configurational and functional cyclohexenol isosters. We demonstrate that the aziridination can be directed by an allylic or homoallylic hydroxyl through H‐bonding and that steric hindrance plays a key role in the diastereoselectivity of the reaction.

show abstract

N-(3,4-dihydro-4-oxoquinazolin-3-yl)pyridmium imides: aziridinating agents for alkenes: measurement of rotational barriers around each N–N bond in an N–N–N system

Cited by 3 publications

References 5 publications

References

References

ChemInform Abstract: N‐(3,4‐Dihydro‐4‐oxoquinazolin‐3‐yl)pyridinium Imides: Aziridinating Agents for Alkenes: Measurement of Rotational Barriers Around Each N‐N Bond in an N‐N‐N System.

Direct Stereoselective Aziridination of Cyclohexenols with 3‐Amino‐2‐(trifluoromethyl)quinazolin‐4(3H)‐one in the Synthesis of Cyclitol Aziridine Glycosidase Inhibitors

Contact Info

Product

Resources

About