123943-98-6Relevant articles and documents
The Chemistry od Erythromycin. Reactions of Erythromycin A Imine and its 6-Methyl Ether with Aldehydes and Hydrazines
Davies, J. Sydney,Hunt, Eric,Zomaya, Iskander I.
, p. 1409 - 1414 (2007/10/02)
Erythromycin imine (3) and its 6-methyl ether (6) are multifunctional N-unsubstituted imines, which, in contrast to most unsubstituted imines, are readily isolable and relatively stable towards hydrolysis.With aldehydes in ethanol, the imines react quite differently: the imine (3) reacts with aliphatic and aromatic aldehydes to give predominantly the 9,11-cyclic imines (9), whereas the ether (6) reacts with aliphatic aldehydes to give N-(1-ethoxyalkyl)imines (13) and with benzaldehyde to give a 9,12-epoxy Schiff's base derivative (12).The imines also differ in their reactivities towards hydrazine derivatives: the imine (3) readily reacts with monosubstituted hydrazines to form erythromycin hydrazone derivatives, whereas the ether (6), in common with erythromycin (1), is unreactive towards these reagents.A rationale for the different modes of reaction of compounds (3) and (6) is discussed.