Photochemistry of the Phthalimide System, 37. Thiazacycloalkanols by Photocyclization of S??Substituted N??(Thioalkyl) phthalimides

Y Sato, H Nakai, M Wada, T Mizoguchi…

Index: Sato, Yasuhiko; Nakai, Hideo; Wada, Masao; Mizoguchi, Tomishige; Hatanaka, Yasumaru; et al. Liebigs Annalen der Chemie, 1985 , # 6 p. 1099 - 1118

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Citation Number: 5

Abstract

Abstract N-Substituted phthalimides (1, 2) possessing a terminal thioether function in their side chain were irradiated with a high-pressure mercury lamp to give a variety of thiazacycloalkanol derivatives (3, 7, 9–13, 16, 17) with favored γ-, δ-, ϵ-, and ζ-hydrogen abstractions (Table 1), in moderate to fairly good yields.

 Related Synthetic Route
2-(methylsulfanylmethyl)isoindole-1,3-dione Structure

20044-28-4

2-(methylsulfan...

~8%

T56 BVNVJ C1 Structure

550-44-7

T56 BVNVJ C1

2-[2-(1,3-dioxoisoindol-2-yl)ethyl]isoindole-1,3-dione Structure

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2-[2-(1,3-dioxo...

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2-(benzylsulfanylmethyl)isoindole-1,3-dione Structure

52096-57-8

2-(benzylsulfan...

~%

T56 BVNVJ C1 Structure

550-44-7

T56 BVNVJ C1

2-[2-(1,3-dioxoisoindol-2-yl)ethyl]isoindole-1,3-dione Structure

607-26-1

2-[2-(1,3-dioxo...

N/A Structure

52096-56-7

N/A

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Potassium phthalimide Structure

1074-82-4

Potassium phtha...

~%

2-[2-(1,3-dioxoisoindol-2-yl)ethyl]isoindole-1,3-dione Structure

607-26-1

2-[2-(1,3-dioxo...

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Chloromethyl Methyl Sulfide Structure

2373-51-5

Chloromethyl Me...

Potassium phthalimide Structure

1074-82-4

Potassium phtha...

~%

2-(methylsulfanylmethyl)isoindole-1,3-dione Structure

20044-28-4

2-(methylsulfan...

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N-carbethoxyphthalimide Structure

22509-74-6

N-carbethoxypht...

S-methyl-DL-cysteine Structure

19651-44-6

S-methyl-DL-cysteine

~%

2-(1,3-dioxoisoindol-2-yl)-3-methylsulfanylpropanoic acid Structure

55582-20-2

2-(1,3-dioxoiso...

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Phthalimide, N-(bromomethyl) Structure

5332-26-3

Phthalimide, N-...

benzylthiol Structure

100-53-8

benzylthiol

~77%

2-(benzylsulfanylmethyl)isoindole-1,3-dione Structure

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2-(benzylsulfan...

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Phthalimide, N-(bromomethyl) Structure

5332-26-3

Phthalimide, N-...

Ethanethiol Structure

75-08-1

Ethanethiol

~84%

2-(ethylsulfanylmethyl)isoindole-1,3-dione Structure

19378-64-4

2-(ethylsulfany...

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2-(3-(METHYLTHIO)PROPYL)ISOINDOLINE-1,3-DIONE Structure

52096-79-4

2-(3-(METHYLTHI...

~56%

2-(3-(METHYLSULFINYL)PROPYL)ISOINDOLINE-1,3-DIONE Structure

98184-57-7

2-(3-(METHYLSUL...

1H-Isoindole-1,3(2H)-dione, 2-[3-(methylsulfonyl)propyl] Structure

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N-(2-Bromoethyl)phthalimide Structure

574-98-1

N-(2-Bromoethyl...

~%

3,4-dihydro-2H-2-benzazepine-1,5-dione Structure

41764-17-4

3,4-dihydro-2H-...

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2-(2-(Isopropylthio)ethyl)-1H-isoindole-1,3(2H)-dione Structure

52096-62-5

2-(2-(Isopropyl...

~17%

N/A Structure

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N/A

3,4-dihydro-2H-2-benzazepine-1,5-dione Structure

41764-17-4

3,4-dihydro-2H-...

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2-(1,3-dioxoisoindol-2-yl)-3-methylsulfanylpropanoic acid Structure

55582-20-2

2-(1,3-dioxoiso...

~10%

N/A Structure

52096-64-7

N/A

3,4-dihydro-2H-2-benzazepine-1,5-dione Structure

41764-17-4

3,4-dihydro-2H-...

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N-carbethoxyphthalimide Structure

22509-74-6

N-carbethoxypht...

~%

3,4-dihydro-2H-2-benzazepine-1,5-dione Structure

41764-17-4

3,4-dihydro-2H-...

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2-(2-(Propylthio)ethyl)-1H-isoindole-1,3(2H)-dione Structure

52096-61-4

2-(2-(Propylthi...

~6%

N/A Structure

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N/A

3,4-dihydro-2H-2-benzazepine-1,5-dione Structure

41764-17-4

3,4-dihydro-2H-...

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2-<2-(Methylthio)ethyl>-1H-isoindole-1,3(2H)-dione Structure

52096-60-3

2-<2-(Methylthi...

~6%

N/A Structure

52096-64-7

N/A

3,4-dihydro-2H-2-benzazepine-1,5-dione Structure

41764-17-4

3,4-dihydro-2H-...

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2-(2-benzylsulfanylethyl)isoindole-1,3-dione Structure

52096-63-6

2-(2-benzylsulf...

~6%

N/A Structure

52096-67-0

N/A

3,4-dihydro-2H-2-benzazepine-1,5-dione Structure

41764-17-4

3,4-dihydro-2H-...

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2-[2-(Cyclohexylthio)ethyl]-1H-isoindole-1,3(2H)-dione Structure

55582-21-3

2-[2-(Cyclohexy...

~5%

3,4-dihydro-2H-2-benzazepine-1,5-dione Structure

41764-17-4

3,4-dihydro-2H-...

N/A Structure

98184-44-2

N/A

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