An Expeditious Synthesis Of 3-Amino B-Lactams Derived From Polyaromatic Compounds

Rhodes²,

Banik³

2013

RSC Adv.

Self Cite

Section: Resultsmentioning

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

A green, chemoselective, and practical approach toward N-(2-azetidinonyl) 2,5-disubstituted pyrroles

Rhodes²,

Banik³

2013

RSC Adv.

Self Cite

“…In all the cases, the reactions are completed within 1–3 min and the products are obtained in excellent yield ( Table 3 ). The 3-amino-2-azetidinones were synthesized following the procedure published from our laboratory [ 63 , 64 ].…”

Section: Resultsmentioning

confidence: 99%

An Expeditious Iodine-Catalyzed Synthesis of 3-Pyrrole-substituted 2-Azetidinones

Cruz²,

Yadav³

et al. 2012

Molecules

Self Cite

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.

“…After completion of the reaction, the reaction mixture was washed with brine and water successively. The organic layer was dried over anhydrous sodium sulfate and the 3-amino β-lactam was isolated in pure form by column chromatography over neutral alumina (methanolic ethyl acetate) in good yield [ 33 ]. The stereochemistry of β-lactams remains unchanged during this conversation.…”

Section: Methodsmentioning

confidence: 99%

Remarkable Iodine-Catalyzed Synthesis of Novel Pyrrole- Bearing N-Polyaromatic β-Lactams

Rivera²,

Salinas³

et al. 2010

Molecules

Self Cite

Because of their interesting biological properties various methods for the synthesis of substituted pyrroles are described in the literature. However, synthesis of pyrroles fused with a β-lactam ring has not been reported. Our group has demonstrated synthesis and biological evaluation of various β-lactams as anticancer agents. The anticancer activities of these compounds have prompted us to study the synthesis of pyrroles bound to the β-lactams. We have identified an expeditious synthetic method for the preparation of pyrroles fused with β-lactams by reacting 3-amino β-lactams with acetonylacetone in the presence of catalytic amounts (5 mol%) of molecular iodine at room temperature. It has also been discovered that the reaction gives products under domestic and automated microwave oven irradiation. To our knowledge, there are no other prior reports that describe the synthesis of pyrrole-substituted β-lactams.