Direct synthesis of magnesium porphine via 1-formyldipyrromethane.
The reaction of 1-formyldipyrromethane (100 mM) in toluene at 115 degrees C containing DBU (10 mol equiv) and MgBr2 (3 mol equiv) in the presence of air affords the magnesium chelate Mg(II) porphine in 30-40% yield. The advantages of the new method include simplicity, high concentration, chromatography-free purification, gram-scale synthesis, and avoidance of the poorly soluble free base porphine. Mg(II) porphine exhibits good solubility in common organic solvents and is a valuable core scaffold for derivatization.
Dogutan
Dilek Kiper
DK
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA.
Ptaszek
Marcin
M
Lindsey
Jonathan S
JS
D008274:Magnesium / Q000737:chemistry*; D008665:Metalloporphyrins / Q000138:chemical synthesis* / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry
C522530:1-formyldipyrromethane; D008665:Metalloporphyrins; D011166:Porphyrins; D011758:Pyrroles; D010165:Palladium; C107018:porphine; D008274:Magnesium; D015032:Zinc; D008697:Methane