Switching between reaction pathways by an alcohol cosolvent effect: SmI2-ethylene glycol vs SmI2-H2O mediated synthesis of uracils.
Org Lett
; 16(21): 5694-7, 2014 Nov 07.
Article
in En
| MEDLINE
| ID: mdl-25343692
ABSTRACT
A chemoselective switch between reaction pathways by an alcohol cosolvent effect in a general SmI2-mediated synthesis of uracil derivatives is described. The method relies on the use of coordinating solvents to increase the redox potential of Sm(II) and results in a chemoselective 1,2-reduction (SmI2-H2O) or 1,2-migration via in situ generated N-acyliminium ions (SmI2-ethylene glycol, EG). This work exploits the mild conditions of the SmI2-mediated monoreduction of barbituric acids and offers an attractive protocol for the synthesis of uracil derivatives with biological activity from readily accessible building blocks.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Samarium
/
Solvents
/
Barbiturates
/
Uracil
/
Ethylene Glycol
/
Alcohols
/
Iodides
/
Ions
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2014
Document type:
Article
Affiliation country:
Estados Unidos