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

Synthèse d'oxopyranno [g] indoles

PT Kim, P Cocolios, R Guilard

Index: Kim, Phieo Ta; Cocolios, Panayotis; Guilard, Roger Canadian Journal of Chemistry, 1982 , vol. 60, p. 2099 - 2103

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Citation Number: 0

Abstract

Reaction of ethyl azidoacetate with 6-formyl-4 chromanones, followed by cyclization of the azides obtained leads to 7, 8-dihydropyrano [2, 3-g] indol-9 (1 H)-one. One aspect of the chemical reactivity of these new tricyclic systems is described. The structure of the compounds isolated from various syntheses is established by proton nmr data.

methoxy-5 oxo-9 dihydro-7,8 pyranno[2,3-g]indolecarboxylate-2 de methyle Structure

methoxy-5 oxo-9...

~90%

Pyrano(2,3-g)indole-2-carboxylic acid, 1,7,8,9-tetrahydro-5-methoxy-9- oxo- Structure

Pyrano(2,3-g)in...

4-Bromo-2-methoxyphenol Structure

4-Bromo-2-metho...

~%

Pyrano(2,3-g)indole-2-carboxylic acid, 1,7,8,9-tetrahydro-5-methoxy-9- oxo- Structure

Pyrano(2,3-g)in...

Guaiacol Structure

~%

Pyrano(2,3-g)indole-2-carboxylic acid, 1,7,8,9-tetrahydro-5-methoxy-9- oxo- Structure

Pyrano(2,3-g)in...

3-(4-bromo-2-methoxyphenoxy)propanoic acid Structure

3-(4-bromo-2-me...

~%

Pyrano(2,3-g)indole-2-carboxylic acid, 1,7,8,9-tetrahydro-5-methoxy-9- oxo- Structure

Pyrano(2,3-g)in...

dioxolanne de la bromo-6 methoxy-8 dihydro-2,3 4H-benzopyranne-1 one-4 Structure

dioxolanne de l...

~%

Pyrano(2,3-g)indole-2-carboxylic acid, 1,7,8,9-tetrahydro-5-methoxy-9- oxo- Structure

Pyrano(2,3-g)in...

dioxolanne-4 methoxy-8 dihydro-2,3 4H-benzopyranne-1 carbaldehyde-6 Structure

dioxolanne-4 me...

~%

Pyrano(2,3-g)indole-2-carboxylic acid, 1,7,8,9-tetrahydro-5-methoxy-9- oxo- Structure

Pyrano(2,3-g)in...

methyl 5-methoxy-7,8-dihydro-1H-spiro[pyrano[2,3-g]indole-9,2'-[1,3]dioxolane]-2-carboxylate Structure

methyl 5-methox...

~%

Pyrano(2,3-g)indole-2-carboxylic acid, 1,7,8,9-tetrahydro-5-methoxy-9- oxo- Structure

Pyrano(2,3-g)in...

bromo-6 methoxy-8 dihydro-2,3 4H-benzopyranne-1 one-4 Structure

bromo-6 methoxy...

~%

Pyrano(2,3-g)indole-2-carboxylic acid, 1,7,8,9-tetrahydro-5-methoxy-9- oxo- Structure

Pyrano(2,3-g)in...

Pyrano(2,3-g)indole-2-carboxylic acid, 1,7,8,9-tetrahydro-5-methoxy-9- oxo- Structure

Pyrano(2,3-g)in...

~54%

acetyl-7 hydroxy-6 methoxy-5 indole Structure

acetyl-7 hydrox...

5-methoxy-7,8-dihydro-1H-pyrano[2,3-g]indol-9-one Structure

5-methoxy-7,8-d...

4-Bromo-2-methoxyphenol Structure

4-Bromo-2-metho...

~%

5-methoxy-7,8-dihydro-1H-pyrano[2,3-g]indol-9-one Structure

5-methoxy-7,8-d...

Guaiacol Structure

~%

5-methoxy-7,8-dihydro-1H-pyrano[2,3-g]indol-9-one Structure

5-methoxy-7,8-d...

3-(4-bromo-2-methoxyphenoxy)propanoic acid Structure

3-(4-bromo-2-me...

~%

5-methoxy-7,8-dihydro-1H-pyrano[2,3-g]indol-9-one Structure

5-methoxy-7,8-d...

dioxolanne de la bromo-6 methoxy-8 dihydro-2,3 4H-benzopyranne-1 one-4 Structure

dioxolanne de l...

~%

5-methoxy-7,8-dihydro-1H-pyrano[2,3-g]indol-9-one Structure

5-methoxy-7,8-d...

dioxolanne-4 methoxy-8 dihydro-2,3 4H-benzopyranne-1 carbaldehyde-6 Structure

dioxolanne-4 me...

~%

5-methoxy-7,8-dihydro-1H-pyrano[2,3-g]indol-9-one Structure

5-methoxy-7,8-d...

methoxy-5 oxo-9 dihydro-7,8 pyranno[2,3-g]indolecarboxylate-2 de methyle Structure

methoxy-5 oxo-9...

~%

5-methoxy-7,8-dihydro-1H-pyrano[2,3-g]indol-9-one Structure

5-methoxy-7,8-d...

methyl 5-methoxy-7,8-dihydro-1H-spiro[pyrano[2,3-g]indole-9,2'-[1,3]dioxolane]-2-carboxylate Structure

methyl 5-methox...

~%

5-methoxy-7,8-dihydro-1H-pyrano[2,3-g]indol-9-one Structure

5-methoxy-7,8-d...

bromo-6 methoxy-8 dihydro-2,3 4H-benzopyranne-1 one-4 Structure

bromo-6 methoxy...

~%

5-methoxy-7,8-dihydro-1H-pyrano[2,3-g]indol-9-one Structure

5-methoxy-7,8-d...