Modified Riemschneider Reaction of 3??Thiocyanatoquinolinediones

O Rudolf, V Mrkvička, A Lyčka, M Rouchal…

Index: Rudolf, Ondrej; Mrkvicka, Vladimir; Lycka, Antonin; Rouchal, Michal; Klasek, Antonin Helvetica Chimica Acta, 2012 , vol. 95, # 8 p. 1352 - 1372

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Citation Number: 2

Abstract

Abstract The Riemschneider reaction of 3-thiocyanatoquinoline-2, 4 (1H, 3H)-diones with conc. H 2 SO 4 was investigated. Using different reaction conditions, 13 types of reaction products were isolated. Compounds bearing a Me, Et, or Bu group at C (3) afforded mainly [1, 3] thiazolo [5, 4-c] quinoline-2, 4-diones and 1, 9b-dihydro-9b-hydroxythiazolo [5, 4-c] quinoline-2, 4-diones. In the case of the 3-Bu derivatives of the starting compounds, C- ...

 Related Synthetic Route
3-ethyl-1,2,3,4-tetrahydro-1-methyl-2,4-dioxoquinolin-3-yl thiocyanate Structure

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3-ethyl-1,2,3,4...

~13%

3-ethyl-1-methyl-4-oxoquinolin-2-olate Structure

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3-ethyl-1-methy...

N/A Structure

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1,2,3,4-tetrahydro-1,3-dimethyl-2,4-dioxoquinolin-3-yl thiocyanate Structure

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~26%

2(1H)-Quinolinone,4-hydroxy-1,3-dimethyl- Structure

32606-02-3

2(1H)-Quinolino...

N/A Structure

1399324-32-3

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N/A Structure

1399324-94-7

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1,2,3,4-tetrahydro-1,3-dimethyl-2,4-dioxoquinolin-3-yl thiocyanate Structure

1399323-83-1

1,2,3,4-tetrahy...

~24%

2(1H)-Quinolinone,4-hydroxy-1,3-dimethyl- Structure

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2(1H)-Quinolino...

N/A Structure

1399324-94-7

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1,2,3,4-tetrahydro-1,3-dimethyl-2,4-dioxoquinolin-3-yl thiocyanate Structure

1399323-83-1

1,2,3,4-tetrahy...

~5%

2(1H)-Quinolinone,4-hydroxy-1,3-dimethyl- Structure

32606-02-3

2(1H)-Quinolino...

N/A Structure

1399324-32-3

N/A

N/A Structure

1399324-73-2

N/A

[1,3]oxathiolo[4,5-c]quinoline-2,4(5H)-dione Structure

1399325-39-3

[1,3]oxathiolo[...

~51%

2,4-Quinolinediol Structure

70254-43-2

2,4-Quinolinediol

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1399323-95-5

N/A

~7%

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1399324-47-0

N/A

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3-ethyl-4-hydro...

2,4(1H,3H)-Quinolinedione, 3-ethyl-3-hydroxy-1-phenyl- Structure

84261-53-0

2,4(1H,3H)-Quin...

3-ethyl-1,2,3,4-tetrahydro-2,4-dioxoquinolin-3-yl thiocyanate Structure

1399323-79-5

3-ethyl-1,2,3,4...

~53%

3-Ethyl-2-hydroxy-4(1H)-quinolinone Structure

1873-60-5

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