Activation of iodosobenzene by catalytic tetrabutylammonium iodide and its application in the oxidation of some isoquinoline alkaloids

WJ Huang, OV Singh, CH Chen, SY Chiou…

Index: Huang, Wei-Jan; Singh, Om V.; Chen, Chung-Hsiung; Chiou, Sheng-You; Lee, Shoei-Sheng Helvetica Chimica Acta, 2002 , vol. 85, # 4 p. 1069 - 1078

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Citation Number: 24

Abstract

Oxidation of N-methyltetrahydroisoquinolines with iodosylbenzene in the presence of a catalytic amount of tetrabutylammonium iodide in various solvents afforded N-methyl-2H-3, 4- dihydroisoquinol-1-ones in almost quantitative yields. The application of this finding to the ...

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6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline Structure

1745-07-9

6,7-Dimethoxy-1...

~29%

6,7-Dimethoxyisoquinoline Structure

15248-39-2

6,7-Dimethoxyis...

6,7-DIMETHOXY-3,4-DIHYDROISOQUINOLIN-1(2H)-ONE Structure

493-49-2

6,7-DIMETHOXY-3...

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline Structure

1745-07-9

6,7-Dimethoxy-1...

~%

6,7-DIMETHOXY-3,4-DIHYDROISOQUINOLIN-1(2H)-ONE Structure

493-49-2

6,7-DIMETHOXY-3...

Dehydroheliamine Structure

3382-18-1

Dehydroheliamine

~%

6,7-Dimethoxyisoquinoline Structure

15248-39-2

6,7-Dimethoxyis...

6,7-DIMETHOXY-3,4-DIHYDROISOQUINOLIN-1(2H)-ONE Structure

493-49-2

6,7-DIMETHOXY-3...

1-(4-bromobenzyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline Structure

78946-22-2

1-(4-bromobenzy...

~86%

1(2H)-Isoquinolinone,3,4-dihydro-6,7-dimethoxy-2-methyl- Structure

6514-05-2

1(2H)-Isoquinol...

Isoquinoline,1,2,3,4-tetrahydro-6,7-dimethoxy-1-[(4-methoxyphenyl)methyl]-2-methyl- Structure

1934-93-6

Isoquinoline,1,...

~85%

1(2H)-Isoquinolinone,3,4-dihydro-6,7-dimethoxy-2-methyl- Structure

6514-05-2

1(2H)-Isoquinol...

1-Benzyl-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-isochinolin Structure

3423-13-0

1-Benzyl-1,2,3,...

~78%

1(2H)-Isoquinolinone,3,4-dihydro-6,7-dimethoxy-2-methyl- Structure

6514-05-2

1(2H)-Isoquinol...

DL-LAUDANOSINE Structure

1699-51-0

DL-LAUDANOSINE

~81%

1(2H)-Isoquinolinone,3,4-dihydro-6,7-dimethoxy-2-methyl- Structure

6514-05-2

1(2H)-Isoquinol...

Isoquinoline,1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl- Structure

16620-96-5

Isoquinoline,1,...

~97%

1(2H)-Isoquinolinone,3,4-dihydro-6,7-dimethoxy-2-methyl- Structure

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1(2H)-Isoquinol...

5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline Structure

94143-83-6

5,6,7,8-tetrahy...

~44%

[1,3]DIOXOLO[4,5-G]ISOQUINOLINE Structure

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[1,3]DIOXOLO[4,...

1,3-Dioxolo[4,5-g]isoquinolin-5(6H)-one,7,8-dihydro- Structure

21796-14-5

1,3-Dioxolo[4,5...

5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline Structure

94143-83-6

5,6,7,8-tetrahy...

~%

[1,3]DIOXOLO[4,5-G]ISOQUINOLINE Structure

269-44-3

[1,3]DIOXOLO[4,...

7,8-Dihydro-1,3-dioxolo[4,5-g]isoquinoline Structure

6882-28-6

7,8-Dihydro-1,3...

~%

[1,3]DIOXOLO[4,5-G]ISOQUINOLINE Structure

269-44-3

[1,3]DIOXOLO[4,...

1,3-Dioxolo[4,5-g]isoquinolin-5(6H)-one,7,8-dihydro- Structure

21796-14-5

1,3-Dioxolo[4,5...

5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline Structure

94143-83-6

5,6,7,8-tetrahy...

~36%

[1,3]DIOXOLO[4,5-G]ISOQUINOLINE Structure

269-44-3

[1,3]DIOXOLO[4,...

1,3-Dioxolo[4,5-g]isoquinolin-5(6H)-one,7,8-dihydro- Structure

21796-14-5

1,3-Dioxolo[4,5...

5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline Structure

94143-83-6

5,6,7,8-tetrahy...

~%

1,3-Dioxolo[4,5-g]isoquinolin-5(6H)-one,7,8-dihydro- Structure

21796-14-5

1,3-Dioxolo[4,5...

7,8-Dihydro-1,3-dioxolo[4,5-g]isoquinoline Structure

6882-28-6

7,8-Dihydro-1,3...

~%

[1,3]DIOXOLO[4,5-G]ISOQUINOLINE Structure

269-44-3

[1,3]DIOXOLO[4,...

1,3-Dioxolo[4,5-g]isoquinolin-5(6H)-one,7,8-dihydro- Structure

21796-14-5

1,3-Dioxolo[4,5...

5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline Structure

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5,6,7,8-tetrahy...

~93%

7,8-Dihydro-1,3-dioxolo[4,5-g]isoquinoline Structure

6882-28-6

7,8-Dihydro-1,3...

Berberine Structure

2086-83-1

Berberine

~4%

8-Oxyberberine Structure

549-21-3

8-Oxyberberine

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6H-Benzo[g]-1,3...

~5%

8-Oxyberberine Structure

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8-Oxyberberine

Berberine Structure

2086-83-1

Berberine

3-[3,4-dihydro-1-oxo-6,7-(methylenedioxy)-2H-isoquinolin-2-yl]-4,5-dimethoxy-1(3H)-isobenzofuranone Structure

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3-[3,4-dihydro-...

Berberine Structure

2086-83-1

Berberine

~%

8-Oxyberberine Structure

549-21-3

8-Oxyberberine

6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine,5,8,13,13a-tetrahydro-9,10-dimethoxy- Structure

29074-38-2

6H-Benzo[g]-1,3...

~%

8-Oxyberberine Structure

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8-Oxyberberine

1,3-Dioxolo[4,5-g]isoquinoline, 5,6,7, 8-tetrahydro-6-methyl- Structure

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1,3-Dioxolo[4,5...

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oxyhydrastinine Structure

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oxyhydrastinine


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