O-H insertion and tandem N-H insertion/cyclization reactions using an iron porphyrin as catalyst with diazo compounds as carbene sources

Autor:	Harun M. Mbuvi, L. Keith Woo, Erik R. Klobukowski, Gina M. Roberts
Rok vydání:	2010
Předmět:	General Chemistry Porphyrin Medicinal chemistry Chloride Catalysis chemistry.chemical_compound chemistry Reagent Tetraphenylporphyrin medicine Organic chemistry Diazo Methylene Carbene medicine.drug
Zdroj:	Journal of Porphyrins and Phthalocyanines. 14:284-292
ISSN:	1099-1409 1088-4246
DOI:	10.1142/s1088424610001982
Popis:	Iron(III) tetraphenylporphyrin chloride, Fe(TPP)Cl , efficiently catalyzed the insertion of carbenes derived from methyl 2-phenyldiazoacetates into O-H bonds of aliphatic and aromatic alcohols, with yields generally above 80%. Although the analogous N-H insertions are rapid at room temperature, the O-H insertion reactions are slower and required heating in refluxing methylene chloride for about 8 hours using 1.0 mol.% catalyst. Fe(TPP)Cl was also found to be effective for tandem N-H insertion/cyclization reactions when 1,2-diamines and 1,2-alcoholamines were treated with diazo reagents to give piperazinones and morpholinones and related analogs such as quinoxalinones and benzoxazin-2-ones. This approach provides a new one-pot route for synthesizing these classes of heterocyclic compounds.
Databáze:	OpenAIRE
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