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Direct synthesis of magnesium porphine via 1-formyldipyrromethane.

ABSTRACT: 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.

SUBMITTER: Dogutan DK

PROVIDER: S-EPMC2532508 | biostudies-literature | 2007 Jun

REPOSITORIES: biostudies-literature

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Direct synthesis of magnesium porphine via 1-formyldipyrromethane.

Dogutan Dilek Kiper DK Ptaszek Marcin M Lindsey Jonathan S JS

The Journal of organic chemistry 20070523 13

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 ...[more]

PMID: 17518498

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