Direct imine acylation: rapid access to diverse heterocyclic scaffolds

TY - JOUR

T1 - Direct imine acylation

T2 - rapid access to diverse heterocyclic scaffolds

AU - Unsworth, William P

AU - Kitsiou, Christiana

AU - Taylor, Richard J K

PY - 2013/1/18

Y1 - 2013/1/18

N2 - A simple and efficient procedure to prepare a range of diverse heterocycles by the direct acylation of imines using a variety of functionalized benzoic acids is described. The methodology features a novel method for N-acyliminium ion generation followed by in situ intramolecular trapping by oxygen-, nitrogen-, sulfur- and carbon-based nucleophiles. Preliminary mechanistic studies, using ReactIR, are also reported.

AB - A simple and efficient procedure to prepare a range of diverse heterocycles by the direct acylation of imines using a variety of functionalized benzoic acids is described. The methodology features a novel method for N-acyliminium ion generation followed by in situ intramolecular trapping by oxygen-, nitrogen-, sulfur- and carbon-based nucleophiles. Preliminary mechanistic studies, using ReactIR, are also reported.

UR - http://www.scopus.com/inward/record.url?scp=84872502575&partnerID=8YFLogxK

U2 - 10.1021/ol303073b

DO - 10.1021/ol303073b

M3 - Article

C2 - 23265307

SN - 1523-7060

VL - 15

SP - 258

EP - 261

JO - Organic Letters

JF - Organic Letters

IS - 2

ER -