Regioselective Transition-Metal-Free Synthesis of 2-(Trimethylsilylmethylene) pyrrol-3-ones by Thermal Cyclization of Acetylenic Enamines

PR Golubev, AS Pankova…

Index: McNab, Hamish; Monahan, Lilian C. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988 , p. 863 - 868

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Citation Number: 4

Abstract

... The Journal of Organic ... 2015, 80 (9), pp 4545–4552. DOI: 10.1021/acs.joc.5b00398. Publication Date (Web): April 20, 2015. Copyright © 2015 American Chemical Society. ... to its stabilization by an intramolecular hydrogen bond, and the (E)/(Z) ratio is ∼1:10 at 20–60 °C. On the ...

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2,2-dimethyl-5-[(2-methyl-1-piperidyl)methylidene]-1,3-dioxane-4,6-dione Structure

89044-58-6

2,2-dimethyl-5-...

~%

5-methyl-6,7,8,8a-tetrahydro-5H-indolizin-1-one Structure

89044-61-1

5-methyl-6,7,8,...

8a-methyl-5,6,7,8-tetrahydroindolizin-1-one Structure

89044-60-0

8a-methyl-5,6,7...

2-Pipecoline Structure

109-05-7

2-Pipecoline

~%

5-methyl-6,7,8,8a-tetrahydro-5H-indolizin-1-one Structure

89044-61-1

5-methyl-6,7,8,...

2,2-dimethyl-5-(5-(5,6-dihydrophenanthridinyl)methylene)-1,3-dioxane-4,6-dione Structure

118060-68-7

2,2-dimethyl-5-...

~42%

Phenanthridine Structure

229-87-8

Phenanthridine

5-(N-N-dibenzyl)-aminomethylene-2,2-dimethyl-1,3-dioxane-4,6-dione Structure

118060-61-0

5-(N-N-dibenzyl...

~51%

1-benzyl-2-phenyl-2H-pyrrol-3-one Structure

118060-73-4

1-benzyl-2-phen...

Dibenzylamine Structure

103-49-1

Dibenzylamine

~%

1-benzyl-2-phenyl-2H-pyrrol-3-one Structure

118060-73-4

1-benzyl-2-phen...

5-(ethoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione Structure

15568-86-2

5-(ethoxymethyl...

2-Pipecoline Structure

109-05-7

2-Pipecoline

~87%

2,2-dimethyl-5-[(2-methyl-1-piperidyl)methylidene]-1,3-dioxane-4,6-dione Structure

89044-58-6

2,2-dimethyl-5-...

5-(N-benzyl-N-phenyl)-aminomethylene-2,2-dimethyl-1,3-dioxane-4,6-dione Structure

118060-62-1

5-(N-benzyl-N-p...

~56%

1,2-diphenyl-2H-pyrrol-3-one Structure

118060-75-6

1,2-diphenyl-2H...

N/A Structure

758640-21-0

N/A

~%

1,2-diphenyl-2H-pyrrol-3-one Structure

118060-75-6

1,2-diphenyl-2H...

5-(ANILINOMETHYLENE)-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE Structure

15568-92-0

5-(ANILINOMETHY...

~%

1-phenyl-2H-pyrrol-3-one Structure

65172-10-3

1-phenyl-2H-pyr...

Structure

74497-02-2

~%

1-phenyl-2H-pyrrol-3-one Structure

65172-10-3

1-phenyl-2H-pyr...

N-Methylaniline Structure

100-61-8

N-Methylaniline

~%

1-phenyl-2H-pyrrol-3-one Structure

65172-10-3

1-phenyl-2H-pyr...

5-(N-methyl-N-t-butyl)-aminomethylene-2,2-dimethyl-1,3-dioxane-4,6-dione Structure

96994-21-7

5-(N-methyl-N-t...

~61%

1-tert-butyl-2H-pyrrol-3-one Structure

96994-20-6

1-tert-butyl-2H...

2,2-dimethyl-5-[(tert-butylamino)methylene]-1,3-dioxane-4,6-dione Structure

118060-67-6

2,2-dimethyl-5-...

~%

1-tert-butyl-2H-pyrrol-3-one Structure

96994-20-6

1-tert-butyl-2H...

n-methyl-tert-butylamine Structure

14610-37-8

n-methyl-tert-b...

~%

1-tert-butyl-2H-pyrrol-3-one Structure

96994-20-6

1-tert-butyl-2H...

5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione Structure

15568-85-1

5-(Methoxymethy...

Dimethylamine Structure

124-40-3

Dimethylamine

~54%

5-(DIMETHYLAMINOMETHYLENE)-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE Structure

75039-60-0

5-(DIMETHYLAMIN...

2,2-dimethyl-5-[(2-methyl-1-piperidyl)methylidene]-1,3-dioxane-4,6-dione Structure

89044-58-6

2,2-dimethyl-5-...

~%

5-methyl-6,7,8,8a-tetrahydro-5H-indolizin-1-one Structure

89044-61-1

5-methyl-6,7,8,...

8a-methyl-5,6,7,8-tetrahydroindolizin-1-one Structure

89044-60-0

8a-methyl-5,6,7...

2-Pipecoline Structure

109-05-7

2-Pipecoline

~%

8a-methyl-5,6,7,8-tetrahydroindolizin-1-one Structure

89044-60-0

8a-methyl-5,6,7...


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