Microwave‐Assisted [3 + 2] Cycloadditions of Azomethine Ylides.

Bashirhiardes, George; Safir, Imad; Mohamed, Achmet Said; Barbot, F.; Laduranty, J.

doi:10.1002/chin.200416129

Cited by 2 publications

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“…The energy is transferred to the molecules before their relaxation, resulting in instantaneous temperature rise at the molecular level that enhances the rates and in many cases the yield by avoiding side reactions. Thus the reactions can be conducted in a very short time period ,− and also under solvent-free conditions …”

Section: Introductionmentioning

confidence: 99%

Intensification and Selectivity Modulation of Ion-Exchange Resin Catalyzed Alkylation of Phenol by Microwave

Ali

Gaikar

2011

Ind. Eng. Chem. Res.

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Microwave irradiation has been used to intensify the alkylation reaction of phenol with tert-butyl alcohol using ionexchange resin as the catalyst. About 86% conversion of phenol is obtained in 4 min under microwave irradiation. The major products are ortho-tert-butyl phenol (o-TBP), para-tert-butyl phenol (p-TBP) and 2,4-di-tert-butyl phenol (2,4-DTBP). o-TBP predominates in the product mixture as the kinetically favored product in shorter reaction times, but p-TBP is the major product for longer reaction times. The selectivity toward ortho-or para-substituted phenols can be manipulated by controlling the exposure time of the reaction mixture to the microwave irradiation. The LangmuirÀHinshelwoodÀHougenÀWatson (LHHW) surface reaction controlled model was used for the kinetic data analysis.

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Section: Introductionmentioning

confidence: 99%

Intensification and Selectivity Modulation of Ion-Exchange Resin Catalyzed Alkylation of Phenol by Microwave

Ali

Gaikar

2011

Ind. Eng. Chem. Res.

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“…Further enhancement of yields for 8 and 9 might be aided by microwave-assisted synthesis as reported by Bashiardes et al in their analysis of synthesis conditions for the [3+2] cycloaddition of azomethine ylides. 88 The microwave increased yields of the major products for most cases by greater than 5 %. SPOPP was confirmed to be 8 by comparing 1 H-NMR spectra obtained to what was reported in literature.…”

Section: Purification and Identification Of The Fused Piperazines Spmentioning

confidence: 96%

Spiropyrrolizidine and piperazine derivatives: Synthesis and evaluation on kras expression levels in human colon cancer cells

Liu¹

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KRAS-driven cancers are notoriously difficult to treat due to poor pharmacodynamics of downstream inhibitors and resistance to anti-EGFR drugs. IMP-1 is a post-transcriptional regulator of KRAS mRNA. As a novel therapeutic approach, the targeting of the IMP-1-KRAS mRNA complex with a spiropyrrolizidine derivative (UNBC152), was studied. LC-MS analysis of UNBC152 indicated presence of impurities. The purpose of this study was to synthesize UNBC152 and determine the responsible bioactive molecule within the impurities. LC-MS and TLC suggested the presence of a bioactive [3+3] cycloaddition side product (SPOPP) in UNBC152. SPOPP suppressed KRAS expression in human colorectal cancer cells. Fluorescence polarization determined that SPOPP did not impact the IMP-1-KRAS mRNA interaction. SPOPP induced G2/M cell cycle arrest as shown by flow cytometry. MTT assay confirmed the SPOPP-induced growth inhibition in SW480 (IC50 = 4.17 μM) and HT29 (IC50 = 6.76 μM). These findings represent a first reporting on the bioactivity of SPOPP. References XIX Chapter 1-Introduction First and foremost, I would like to thank my supervisor, Dr. Chow Lee for giving me the opportunity to work in an excellent cancer research lab. Your support and guidance throughout the past few years have helped me grow substantially as a researcher. I would never forget the time spent in this lab, as it also helped me grow personally. To Dr. Tina Bott, my co-supervisor, I would like to thank you for your patience. You have always been a great mentor for organic chemistry, from undergrad till now. Your help has been tremendous, especially during the initial syntheses. To Dr. Maggie Li, thank you for joining me on the front lines in the assay screens to help solve the UNBC152 puzzle. You always had wise words during my quandaries. I would like to acknowledge Dr. Kerry Reimer for passing on excellent theoretical knowledge for HPLC purifications. I would like to acknowledge Dr. Guy Plourde for always inspiring me to think about the mechanistic nature of reactions. I would like to thank Dr. Hossein Kazemian for being a gracious host of the Northern Analytical Lab. Thank you to Charles Bradshaw for keeping the HPLC running. To Dr. Liz Dunn and Dr. Kaila Fadock, thank you for the technical knowledge on NMR. To Sebastian and Corbin, thank you for all the great times in and out of the lab; I am fortunate to have met the both of you. To my other close friends, Cale, Laura, Levon, Jonah, Aaron and Joshua, thank you for always being around, even when I seemingly drop of the face of the Earth to do research. Last but not least, I would like to thank my parents. To my mother Kit Pang, thank you for always believing in me, especially when I was meandering through different educational paths. To my late father, David Liu, thank you for supporting me throughout the years. I miss you more than you would ever know.

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Microwave‐Assisted [3 + 2] Cycloadditions of Azomethine Ylides.

Cited by 2 publications

References 1 publication

Intensification and Selectivity Modulation of Ion-Exchange Resin Catalyzed Alkylation of Phenol by Microwave

Intensification and Selectivity Modulation of Ion-Exchange Resin Catalyzed Alkylation of Phenol by Microwave

Spiropyrrolizidine and piperazine derivatives: Synthesis and evaluation on kras expression levels in human colon cancer cells

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