Modular, gold-catalyzed approach to the synthesis of lead-like piperazine scaffolds.
Ring-opening of cyclic sulfamidates with propargylic sulfonamides yielded substrates for a gold-catalyzed cyclization to yield tetrahydropyrazines. Manipulation of the tetrahydropyrazines, by reduction or using multicomponent reactions, yielded piperazine scaffolds in which substitution of the carbon atoms was varied. Such scaffolds may have value in the synthesis of novel screening compounds with lead-like molecular properties.
School of Chemistry and Astbury Centre for Structural Molecular Biology, University of Leeds , LS2 9JT Leeds, U.K. , and AstraZeneca, Mereside, Alderley Park, Macclesfield, Cheshire SK10 4TG, U.K.
Thomas
T
James
Iain
I
Simpson
J Andrew
JA
Grant
Visuvanathar
V
Sridharan
Adam
A
Nelson
D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry; D013449:Sulfonamides / Q000737:chemistry*
D010879:Piperazines; D013449:Sulfonamides; D006046:Gold