Titanium(IV) isopropoxide mediated synthesis of pyrimidin-4-ones.
A novel, one-step method for the synthesis of tri- and tetrasubstituted pyrimidin-4-ones is reported. This method involves a titanium(IV)-mediated cyclization involving two sequential condensations of primary and beta-ketoamides. The reaction is operationally facile, readily scalable, and offers rapid entry into differentially substituted pyrimidin-4-one scaffolds. The high functional group compatibility allows for substantial diversification in the products generated from this transformation.
Ramanjulu
Joshi M
JM
Department of Medicinal Chemistry, Immuno-Inflamation CEDD, GlaxoSmithKline, 1250 South Collegeville Road, Collegeville, Pennsylvania 19426, USA. joshi.m.ramanjulu@gsk.com
Demartino
Michael P
MP
Lan
Yunfeng
Y
Marquis
Robert
R
D002384:Catalysis; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011744:Pyrimidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D009942:Organometallic Compounds; D011744:Pyrimidinones; C102815:titanium isopropoxide