An expeditious iodine-catalyzed synthesis of 3-pyrrole-substituted 2-azetidinones.
Molecules
; 17(10): 11570-84, 2012 Sep 28.
Article
em En
| MEDLINE
| ID: mdl-23023683
ABSTRACT
2-Azetidinones and pyrroles are two highly important classes of molecules in organic and medicinal chemistry. A green and practical method for the synthesis of 3-pyrrole-substituted 2-azetidinones using catalytic amounts of molecular iodine under microwave irradiation has been developed. Following this method, a series of 3-pyrrole- substituted 2-azetidinones have been synthesized with a variety of substituents at N-1 and at C-4. The procedure is equally effective for mono- as well as polyaromatic groups at the N-1 position of the 2-azetidinone ring. The C-4 substituent has no influence either on the yield or the rate of the reaction. Optically pure 3-pyrrole-substituted 2-azetidinones have also been synthesized following this methodology. No deprotection/rearrangement has been identified in this process, even with highly acid sensitive group-containing substrates. A plausible mechanistic pathway has also been suggested based on the evidence obtained from ¹H-NMR spectroscopy. The extreme rapidity with excellent reaction yields is believed to be the result of a synergistic effect of the Lewis acid catalyst (molecular iodine) and microwave irradiation.
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1
Base de dados:
MEDLINE
Assunto principal:
Azetidinas
/
Iodo
Idioma:
En
Ano de publicação:
2012
Tipo de documento:
Article