e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Pyrolysis of alkyl 2-or 6-alkoxynicotinates. An unexpected decarbalkoxylation reaction

GR Newkome, DK Kohli, T Kawato

Index: Newkome, George R.; Kohli, Dalip K.; Kawato, Toshio Journal of Organic Chemistry, 1980 , vol. 45, # 22 p. 4508 - 4511

Full Text: HTML

Citation Number: 6

Abstract

of 3 and 4 show that fluorinated methylcholanthrenes containing fluorine in the angular benzene ring can be readily prepared. However, the failures to produce 11-fluoro-3- methylcholanthrene5 and 12-fluoro-3-methylcholanthrene (this paper) show that alternate synthetic schemes to the Elbs route must be developed. The failure to prepare the 10- methoxy compound parallels the failure to produce the 11-methoxy compound previously ...

Ethyl 2-ethoxynicotinate Structure

Ethyl 2-ethoxyn...

~92%

2(1H)-PYRIDINONE, 1-ETHYL Structure

2(1H)-PYRIDINON...

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Ethyl-1-ethyl-1,6-dihydro-6-oxopyridin-3-carboxylat Structure

Ethyl-1-ethyl-1...

~91%

2(1H)-PYRIDINONE, 1-ETHYL Structure

2(1H)-PYRIDINON...

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3-Pyridinecarboxylicacid, 6-methoxy-, ethyl ester Structure

3-Pyridinecarbo...

~%

N-Methyl-2-pyridone Structure

N-Methyl-2-pyridone

2(1H)-PYRIDINONE, 1-ETHYL Structure

2(1H)-PYRIDINON...

1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid methyl ester Structure

1-Methyl-6-oxo-...

Detail Learn More

3-Pyridinecarboxylicacid, 6-methoxy-, ethyl ester Structure

3-Pyridinecarbo...

~%

N-Methyl-2-pyridone Structure

N-Methyl-2-pyridone

2(1H)-PYRIDINONE, 1-ETHYL Structure

2(1H)-PYRIDINON...

3-Pyridinecarboxylicacid, 1,6-dihydro-1-methyl-6-oxo-, ethyl ester Structure

3-Pyridinecarbo...

Detail Learn More

Ethyl 2-ethoxynicotinate Structure

Ethyl 2-ethoxyn...

~%

2(1H)-PYRIDINONE, 1-ETHYL Structure

2(1H)-PYRIDINON...

1-ethyl-3-carbethoxy-2(1H)-pyridinone Structure

1-ethyl-3-carbe...

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ethyl 6-ethoxynicotinate Structure

ethyl 6-ethoxyn...

~%

2(1H)-PYRIDINONE, 1-ETHYL Structure

2(1H)-PYRIDINON...

Ethyl-1-ethyl-1,6-dihydro-6-oxopyridin-3-carboxylat Structure

Ethyl-1-ethyl-1...

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3-Pyridinecarboxylicacid, 6-methoxy-, ethyl ester Structure

3-Pyridinecarbo...

~%

N-Methyl-2-pyridone Structure

N-Methyl-2-pyridone

2(1H)-PYRIDINONE, 1-ETHYL Structure

2(1H)-PYRIDINON...

1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid methyl ester Structure

1-Methyl-6-oxo-...

Detail Learn More

methyl 6-ethoxynicotinate Structure

methyl 6-ethoxy...

~%

N-Methyl-2-pyridone Structure

N-Methyl-2-pyridone

2(1H)-PYRIDINONE, 1-ETHYL Structure

2(1H)-PYRIDINON...

1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid methyl ester Structure

1-Methyl-6-oxo-...

Detail Learn More

METHYL 6-OXO-1,6-DIHYDRO-3-PYRIDINECARBOXYLATE Structure

METHYL 6-OXO-1,...

~%

3-Pyridinecarboxylicacid, 1,6-dihydro-1-methyl-6-oxo-, ethyl ester Structure

3-Pyridinecarbo...

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3-Pyridinecarboxylicacid, 6-methoxy-, ethyl ester Structure

3-Pyridinecarbo...

~%

N-Methyl-2-pyridone Structure

N-Methyl-2-pyridone

2(1H)-PYRIDINONE, 1-ETHYL Structure

2(1H)-PYRIDINON...

1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid methyl ester Structure

1-Methyl-6-oxo-...

Detail Learn More

3-Pyridinecarboxylicacid, 6-methoxy-, ethyl ester Structure

3-Pyridinecarbo...

~%

N-Methyl-2-pyridone Structure

N-Methyl-2-pyridone

2(1H)-PYRIDINONE, 1-ETHYL Structure

2(1H)-PYRIDINON...

3-Pyridinecarboxylicacid, 1,6-dihydro-1-methyl-6-oxo-, ethyl ester Structure

3-Pyridinecarbo...

Detail Learn More

methyl 6-ethoxynicotinate Structure

methyl 6-ethoxy...

~%

1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid methyl ester Structure

1-Methyl-6-oxo-...

3-Pyridinecarboxylicacid, 1,6-dihydro-1-methyl-6-oxo-, ethyl ester Structure

3-Pyridinecarbo...

Ethyl-1-ethyl-1,6-dihydro-6-oxopyridin-3-carboxylat Structure

Ethyl-1-ethyl-1...

Detail Learn More

3-Pyridinecarboxylicacid, 6-methoxy-, ethyl ester Structure

3-Pyridinecarbo...

~%

N-Methyl-2-pyridone Structure

N-Methyl-2-pyridone

2(1H)-PYRIDINONE, 1-ETHYL Structure

2(1H)-PYRIDINON...

1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid methyl ester Structure

1-Methyl-6-oxo-...

Detail Learn More

methyl 6-ethoxynicotinate Structure

methyl 6-ethoxy...

~%

N-Methyl-2-pyridone Structure

N-Methyl-2-pyridone

2(1H)-PYRIDINONE, 1-ETHYL Structure

2(1H)-PYRIDINON...

1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid methyl ester Structure

1-Methyl-6-oxo-...

Detail Learn More

METHYL 6-OXO-1,6-DIHYDRO-3-PYRIDINECARBOXYLATE Structure

METHYL 6-OXO-1,...

~%

1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid methyl ester Structure

1-Methyl-6-oxo-...

Learn More

3-Pyridinecarboxylicacid, 6-methoxy-, ethyl ester Structure

3-Pyridinecarbo...

~%

N-Methyl-2-pyridone Structure

N-Methyl-2-pyridone

2(1H)-PYRIDINONE, 1-ETHYL Structure

2(1H)-PYRIDINON...

1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid methyl ester Structure

1-Methyl-6-oxo-...

Detail Learn More

methyl 6-ethoxynicotinate Structure

methyl 6-ethoxy...

~%

1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid methyl ester Structure

1-Methyl-6-oxo-...

3-Pyridinecarboxylicacid, 1,6-dihydro-1-methyl-6-oxo-, ethyl ester Structure

3-Pyridinecarbo...

Ethyl-1-ethyl-1,6-dihydro-6-oxopyridin-3-carboxylat Structure

Ethyl-1-ethyl-1...

Detail Learn More

3-Pyridinecarboxylicacid, 6-methoxy-, ethyl ester Structure

3-Pyridinecarbo...

~%

N-Methyl-2-pyridone Structure

N-Methyl-2-pyridone

2(1H)-PYRIDINONE, 1-ETHYL Structure

2(1H)-PYRIDINON...

1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid methyl ester Structure

1-Methyl-6-oxo-...

Detail Learn More

methyl 6-ethoxynicotinate Structure

methyl 6-ethoxy...

~%

N-Methyl-2-pyridone Structure

N-Methyl-2-pyridone

2(1H)-PYRIDINONE, 1-ETHYL Structure

2(1H)-PYRIDINON...

1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid methyl ester Structure

1-Methyl-6-oxo-...

Detail Learn More

Methyl 2-methoxynicotinate Structure

Methyl 2-methox...

~%

methyl 1-methyl-2-oxopyridine-3-carboxylate Structure

methyl 1-methyl...

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Methyl 2-methoxynicotinate Structure

Methyl 2-methox...

~74%

N-Methyl-2-pyridone Structure

N-Methyl-2-pyridone

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Relative reactivities of heteroaromatic cations toward ferri...

[Bunting, John W.; Stefanidis, Dimitrios Journal of Organic Chemistry, 1986 , vol. 51, # 11 p. 2068 - 2071]

Micellar effects upon the reaction of hydroxide ion with N-a...

[Al-Lohedan, Hamad A.; Bunton, Clifford A.; Romsted, Laurence S. Journal of Organic Chemistry, 1982 , vol. 47, # 18 p. 3528 - 3532]