Cycloaddition routes to azaanthraquinone derivatives. 1. Use of azadienophiles

T Potts, D Bhattacharjee, EB Walsh

Index: Potts, Kevin T.; Bhattacharjee, Debkumar; Walsh, Eileen B. Journal of Organic Chemistry, 1986 , vol. 51, # 11 p. 2011 - 2021

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Citation Number: 48

Abstract

The mono-and diazanaphthoquinones underwent facile cycloaddition with cyclic and alicyclic dienes, and in the majority of these cycloadditions the initial 1: l-cycloadducts or their tautomers and intermediate products formed in the oxidation procedure leading to the final azaanthraquinones were isolated. Quinoline-5, 8-dione and l-methoxy-l, 3- cyclohexadiene gave the 8-methoxy isomer in an essentially regiospecific cycloaddition; ...

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5,8-QUINOLINEQUINONE Structure

10470-83-4

5,8-QUINOLINEQUINONE

trans,trans-1,4-diacetoxy-1,3-butadiene Structure

15910-11-9

trans,trans-1,4...

~84%

benzo[g]quinoline-5,10-dione Structure

3712-09-2

benzo[g]quinoli...

6,9-dihydro-6,9-ethanobenzoquinoline Structure

13785-27-8

6,9-dihydro-6,9...

~73%

benzo[g]quinoline-5,10-dione Structure

3712-09-2

benzo[g]quinoli...

5,8-QUINOLINEQUINONE Structure

10470-83-4

5,8-QUINOLINEQUINONE

1-acetoxy-1,3-butadiene Structure

1515-76-0

1-acetoxy-1,3-b...

~67%

benzo[g]quinoline-5,10-dione Structure

3712-09-2

benzo[g]quinoli...

5,8-QUINOLINEQUINONE Structure

10470-83-4

5,8-QUINOLINEQUINONE

~%

benzo[g]quinoline-5,10-dione Structure

3712-09-2

benzo[g]quinoli...

N/A Structure

101402-59-9

N/A

~%

benzo[g]quinoline-5,10-dione Structure

3712-09-2

benzo[g]quinoli...

Isoquinoline Structure

119-65-3

Isoquinoline

~%

isoquinoline-5,8-dione Structure

50-46-4

isoquinoline-5,...

2-chloro-5,8-dihydroxy-4-methylquinoline Structure

101402-57-7

2-chloro-5,8-di...

~93%

2-chloro-4-methylquinoline-5,8-dione Structure

101402-58-8

2-chloro-4-meth...

2-Pyridinecarboxaldehyde Structure

1121-60-4

2-Pyridinecarbo...

N,N-diethyl-3-methoxybenzamide Structure

62924-93-0

N,N-diethyl-3-m...

~%

9-methoxybenzo[g]quinoline-5,10-dione Structure

90381-59-2

9-methoxybenzo[...

N/A Structure

101402-59-9

N/A

~80%

6,9-dihydro-6,9-ethanobenzoquinoline Structure

13785-27-8

6,9-dihydro-6,9...

5,8-QUINOLINEQUINONE Structure

10470-83-4

5,8-QUINOLINEQUINONE

~%

6,9-dihydro-6,9-ethanobenzoquinoline Structure

13785-27-8

6,9-dihydro-6,9...

N/A Structure

906723-97-5

N/A

~41%

6-methoxybenzo[g]isoquinoline-5,10-dione Structure

90381-62-7

6-methoxybenzo[...

Isoquinoline Structure

119-65-3

Isoquinoline

~%

6-methoxybenzo[g]isoquinoline-5,10-dione Structure

90381-62-7

6-methoxybenzo[...

Isoquinolin-5-amine Structure

1125-60-6

Isoquinolin-5-amine

~%

6-methoxybenzo[g]isoquinoline-5,10-dione Structure

90381-62-7

6-methoxybenzo[...

5-Nitroisoquinoline Structure

607-32-9

5-Nitroisoquinoline

~%

6-methoxybenzo[g]isoquinoline-5,10-dione Structure

90381-62-7

6-methoxybenzo[...

ISOQUINOLINE-5,8-DIAMINE Structure

1127-49-7

ISOQUINOLINE-5,...

~%

6-methoxybenzo[g]isoquinoline-5,10-dione Structure

90381-62-7

6-methoxybenzo[...

isoquinoline-5,8-dione Structure

50-46-4

isoquinoline-5,...

~%

6-methoxybenzo[g]isoquinoline-5,10-dione Structure

90381-62-7

6-methoxybenzo[...

p-Formylpyridine Structure

872-85-5

p-Formylpyridine

Benzamide,N,N-diethyl-2-methoxy- Structure

51674-10-3

Benzamide,N,N-d...

~%

6-methoxybenzo[g]isoquinoline-5,10-dione Structure

90381-62-7

6-methoxybenzo[...

6,10-dione,6,9-dihydro Structure

96937-79-0

6,10-dione,6,9-...

~79%

Benz[g]isoquinoline-5,10-dione Structure

46492-08-4

Benz[g]isoquino...

Isoquinoline Structure

119-65-3

Isoquinoline

~%

Benz[g]isoquinoline-5,10-dione Structure

46492-08-4

Benz[g]isoquino...

Isoquinolin-5-amine Structure

1125-60-6

Isoquinolin-5-amine

~%

Benz[g]isoquinoline-5,10-dione Structure

46492-08-4

Benz[g]isoquino...

5-Nitroisoquinoline Structure

607-32-9

5-Nitroisoquinoline

~%

Benz[g]isoquinoline-5,10-dione Structure

46492-08-4

Benz[g]isoquino...

ISOQUINOLINE-5,8-DIAMINE Structure

1127-49-7

ISOQUINOLINE-5,...

~%

Benz[g]isoquinoline-5,10-dione Structure

46492-08-4

Benz[g]isoquino...

isoquinoline-5,8-dione Structure

50-46-4

isoquinoline-5,...

~%

Benz[g]isoquinoline-5,10-dione Structure

46492-08-4

Benz[g]isoquino...

isoquinoline-5,8-dione Structure

50-46-4

isoquinoline-5,...

trans,trans-1,4-diacetoxy-1,3-butadiene Structure

15910-11-9

trans,trans-1,4...

~%

Benz[g]isoquinoline-5,10-dione Structure

46492-08-4

Benz[g]isoquino...


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