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2. Microwave-Enhanced Organic Syntheses for the Undergraduate Laboratory: Diels-Alder Cycloaddition, Wittig Reaction, and Williamson Ether Synthesis

Author

Baar, Marsha R., Falcone, Danielle, and Gordon, Christopher

Abstract

Microwave heating enhanced the rate of three reactions typically performed in our undergraduate organic chemistry laboratory: a Diels-Alder cycloaddition, a Wittig salt formation, and a Williamson ether synthesis. Ninety-minute refluxes were shortened to 10 min using a laboratory-grade microwave oven. In addition, yields improved for the Wittig salt and ether preparations. The Diels-Alder cycloaddition of "N"-phenylmaleimide and 1,3-cyclohexadiene in absolute ethanol in a closed vessel and 130 [degree]C gave 84-90% yields. Formation of the Wittig salt, benzyltriphenylphosphonium chloride, from triphenylphosphine and benzyl chloride gave yields greater than 90% when heated in acetonitrile at 200 [degree]C Yields doubled in the Williamson ether synthesis of 2-ethoxynaphthalene, from 2-naphthol, methanolic potassium hydroxide, and iodoethane with microwave heating at 130 [degree]C. (Contains 1 table and 7 notes.)

Published
2010
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4. Microwave-enhanced organic syntheses for the undergraduate laboratory: Diels-Alder cycloaddition, Wittig reaction, and Williamson ether synthesis

Author

Baar, Marsha R., Falcone, Danielle, and Gordon, Christopher

Subjects
Microwave heating -- Usage, Organic compounds -- Synthesis, Organic compounds -- Tests, problems and exercises, Chemistry, Education, Science and technology
Abstract

An undergraduate laboratory demonstration present how microwave heating safely improves the rates of a Diels-Alder cycloaddition, Wittig reaction, and Williamson ether synthesis. The exercise led to higher yields without a major redesign of the conditions in the reactions. Microwave heating also resulted in time savings and less electric consumption.

Published
2010

7. Discovery of 1-[3-(1-Methyl-1H-pyrazol-4-yl)-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl]-N-(pyridin-2-ylmethyl)methanesulfonamide (MK-8033): A Specific c-Met/Ron Dual Kinase Inhibitor with Preferential Affinity for the Activated State of c-Met

Author

Northrup, Alan B., primary, Katcher, Matthew H., additional, Altman, Michael D., additional, Chenard, Melissa, additional, Daniels, Matthew H., additional, Deshmukh, Sujal V., additional, Falcone, Danielle, additional, Guerin, David J., additional, Hatch, Harold, additional, Li, Chaomin, additional, Lu, Wei, additional, Lutterbach, Bart, additional, Allison, Timothy J., additional, Patel, Sangita B., additional, Reilly, John F., additional, Reutershan, Michael, additional, Rickert, Keith W., additional, Rosenstein, Craig, additional, Soisson, Stephen M., additional, Szewczak, Alexander A., additional, Walker, Deborah, additional, Wilson, Kevin, additional, Young, Jonathan R., additional, Pan, Bo-Sheng, additional, and Dinsmore, Christopher J., additional

Published
2013
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9. Discovery of a 5H-Benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (MK-2461) Inhibitor of c-Met Kinase for the Treatment of Cancer

Author

Katz, Jason D., primary, Jewell, James P., additional, Guerin, David J., additional, Lim, Jongwon, additional, Dinsmore, Christopher J., additional, Deshmukh, Sujal V., additional, Pan, Bo-Sheng, additional, Marshall, C. Gary, additional, Lu, Wei, additional, Altman, Michael D., additional, Dahlberg, William K., additional, Davis, Lenora, additional, Falcone, Danielle, additional, Gabarda, Ana E., additional, Hang, Gaozhen, additional, Hatch, Harold, additional, Holmes, Rachael, additional, Kunii, Kaiko, additional, Lumb, Kevin J., additional, Lutterbach, Bart, additional, Mathvink, Robert, additional, Nazef, Naim, additional, Patel, Sangita B., additional, Qu, Xianlu, additional, Reilly, John F., additional, Rickert, Keith W., additional, Rosenstein, Craig, additional, Soisson, Stephen M., additional, Spencer, Kerrie B., additional, Szewczak, Alexander A., additional, Walker, Deborah, additional, Wang, Wenxian, additional, Young, Jonathan, additional, and Zeng, Qinwen, additional

Published
2011
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11. Discoveryof 1-[3-(1-Methyl-1H-pyrazol-4-yl)-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl]-N-(pyridin-2-ylmethyl)methanesulfonamide(MK-8033): A Specific c-Met/Ron Dual Kinase Inhibitor withPreferential Affinity for the Activated State of c-Met.

Author

Northrup, Alan B., Katcher, Matthew H., Altman, Michael D., Chenard, Melissa, Daniels, Matthew H., Deshmukh, Sujal V., Falcone, Danielle, Guerin, David J., Hatch, Harold, Li, Chaomin, Lu, Wei, Lutterbach, Bart, Allison, Timothy J., Patel, Sangita B., Reilly, John F., Reutershan, Michael, Rickert, Keith W., Rosenstein, Craig, Soisson, Stephen M., and Szewczak, Alexander A.

Published
2013
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