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

3, 4??Dihydro??2??phenyl??2H??pyrano [2, 3??b] pyridines. Novel aza analogs of flavans

TM Bargar, T Wilson, JK Daniel

Index: Bargar, T. M.; Wilson, T.; Daniel, J. K. Journal of Heterocyclic Chemistry, 1985 , vol. 22, p. 1583 - 1592

Full Text: HTML

Citation Number: 14

Abstract

Abstract Complementary approaches to the synthesis of the title compounds 1 are described. Metallation of 3, 5-di-bromo-2-methoxypyridine (5b) by bromine/lithium exchange gave selectively the 3-lithio intermediate 6 which was trapped with substituted cinnamaldehydes 7, providing allylic alcohols 8 in good yields. Methyl ether cleavage and concomitant cyclization occurred on exposure to concentrated hydrobromic acid in hot ...

5-Chloro-2-methoxypyridine Structure

5-Chloro-2-meth...

~%

6-chloro-2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-chloro-2-(3,4...

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3-Bromo-5-chloro-2-methoxypyridine Structure

3-Bromo-5-chlor...

~%

6-chloro-2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-chloro-2-(3,4...

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N/A Structure

~%

6-chloro-2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-chloro-2-(3,4...

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2,5-Dichloropyridine Structure

2,5-Dichloropyridine

~%

6-chloro-2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-chloro-2-(3,4...

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5-Chloro-2-methoxypyridine Structure

5-Chloro-2-meth...

~%

6-chloro-2-(4-chlorophenyl)-2H-pyrano[2,3-b]pyridine Structure

6-chloro-2-(4-c...

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3-Bromo-5-chloro-2-methoxypyridine Structure

3-Bromo-5-chlor...

~%

6-chloro-2-(4-chlorophenyl)-2H-pyrano[2,3-b]pyridine Structure

6-chloro-2-(4-c...

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2,5-Dichloropyridine Structure

2,5-Dichloropyridine

~%

6-chloro-2-(4-chlorophenyl)-2H-pyrano[2,3-b]pyridine Structure

6-chloro-2-(4-c...

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(E)-5-Bromo-α-[2-(3,4-dichlorophenyl)ethenyl]-2-methoxy-3-pyridinemethanol Structure

(E)-5-Bromo-α-[...

~86%

6-bromo-2-(3,4-dichlorophenyl)-2H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

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2-Methoxypyridine Structure

2-Methoxypyridine

~%

6-bromo-2-(3,4-dichlorophenyl)-2H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

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(E)-3-(5-bromo-2-methoxypyridin-3-yl)-1-(3,4-dichlorophenyl)prop-2-en-1-ol Structure

(E)-3-(5-bromo-...

~%

6-bromo-2-(3,4-dichlorophenyl)-2H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

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5-BROMO-2-METHOXY-PYRIDINE-3-CARBALDEHYDE Structure

5-BROMO-2-METHO...

~%

6-bromo-2-(3,4-dichlorophenyl)-2H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

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1-(3,4-dichlorophenyl)ethanone Structure

1-(3,4-dichloro...

~%

6-bromo-2-(3,4-dichlorophenyl)-2H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

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3,5-Dibromo-2-methoxypyridine Structure

3,5-Dibromo-2-m...

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~%

5-Bromo-6-methoxynicotinaldehyde Structure

5-Bromo-6-metho...

5-BROMO-2-METHOXY-PYRIDINE-3-CARBALDEHYDE Structure

5-BROMO-2-METHO...

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3-Bromo-5-chloro-2-methoxypyridine Structure

3-Bromo-5-chlor...

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~%

5-Bromo-6-methoxynicotinaldehyde Structure

5-Bromo-6-metho...

5-Chloro-2-methoxynicotinaldehyde Structure

5-Chloro-2-meth...

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3,5-Dibromo-2-methoxypyridine Structure

3,5-Dibromo-2-m...

~%

6-bromo-2-(3,4-dichlorophenyl)-2H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

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6-bromo-2-(3,4-dichlorophenyl)-2H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

~79%

6-bromo-2-(3,4-dichlorophenyl)-4H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

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2-Methoxypyridine Structure

2-Methoxypyridine

~%

6-bromo-2-(3,4-dichlorophenyl)-4H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

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3,5-Dibromo-2-methoxypyridine Structure

3,5-Dibromo-2-m...

~%

6-bromo-2-(3,4-dichlorophenyl)-4H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

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(E)-5-Bromo-α-[2-(3,4-dichlorophenyl)ethenyl]-2-methoxy-3-pyridinemethanol Structure

(E)-5-Bromo-α-[...

~%

6-bromo-2-(3,4-dichlorophenyl)-4H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

Learn More

5-BROMO-2-METHOXY-PYRIDINE-3-CARBALDEHYDE Structure

5-BROMO-2-METHO...

~%

6-bromo-2-(3,4-dichlorophenyl)-4H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

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(E)-3-(5-Bromo-2-methoxy-3-pyridinyl)-1-(3,4-dichlorophenyl)-2-propen-1-one Structure

(E)-3-(5-Bromo-...

~%

6-bromo-2-(3,4-dichlorophenyl)-4H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

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(E)-3-(5-bromo-2-methoxypyridin-3-yl)-1-(3,4-dichlorophenyl)prop-2-en-1-ol Structure

(E)-3-(5-bromo-...

~%

6-bromo-2-(3,4-dichlorophenyl)-4H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

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1-(3,4-dichlorophenyl)ethanone Structure

1-(3,4-dichloro...

~%

6-bromo-2-(3,4-dichlorophenyl)-4H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

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2-Methoxypyridine Structure

2-Methoxypyridine

~0%

2-Methoxy-5-Bromopyridine Structure

2-Methoxy-5-Bro...

3,5-Dibromo-2-methoxypyridine Structure

3,5-Dibromo-2-m...

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2-Methoxypyridine Structure

2-Methoxypyridine

~70%

2-Methoxy-5-Bromopyridine Structure

2-Methoxy-5-Bro...

3,5-Dibromo-2-methoxypyridine Structure

3,5-Dibromo-2-m...

Learn More

5-Chloro-2-methoxypyridine Structure

5-Chloro-2-meth...

~%

6-chloro-2-(4-chlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-chloro-2-(4-c...

Learn More

3-Bromo-5-chloro-2-methoxypyridine Structure

3-Bromo-5-chlor...

~%

6-chloro-2-(4-chlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-chloro-2-(4-c...

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(E)-5-Chloro-α-(2-(4-chlorophenyl)ethenyl)-2-methoxy-3-pyridinemethanol Structure

(E)-5-Chloro-α-...

~%

6-chloro-2-(4-chlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-chloro-2-(4-c...

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2,5-Dichloropyridine Structure

2,5-Dichloropyridine

~%

6-chloro-2-(4-chlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-chloro-2-(4-c...

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2-Methoxypyridine Structure

2-Methoxypyridine

~%

6-bromo-2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

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3,5-Dibromo-2-methoxypyridine Structure

3,5-Dibromo-2-m...

~%

6-bromo-2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

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(E)-5-Bromo-α-[2-(3,4-dichlorophenyl)ethenyl]-2-methoxy-3-pyridinemethanol Structure

(E)-5-Bromo-α-[...

~%

6-bromo-2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

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5-BROMO-2-METHOXY-PYRIDINE-3-CARBALDEHYDE Structure

5-BROMO-2-METHO...

~%

6-bromo-2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

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(E)-3-(5-bromo-2-methoxypyridin-3-yl)-1-(3,4-dichlorophenyl)prop-2-en-1-ol Structure

(E)-3-(5-bromo-...

~%

6-bromo-2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

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1-(3,4-dichlorophenyl)ethanone Structure

1-(3,4-dichloro...

~%

6-bromo-2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

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2-Methoxypyridine Structure

2-Methoxypyridine

~%

2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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3,5-Dibromo-2-methoxypyridine Structure

3,5-Dibromo-2-m...

~%

2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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6-bromo-2-(3,4-dichlorophenyl)-2H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

~%

2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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(E)-5-Bromo-α-[2-(3,4-dichlorophenyl)ethenyl]-2-methoxy-3-pyridinemethanol Structure

(E)-5-Bromo-α-[...

~%

2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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5-BROMO-2-METHOXY-PYRIDINE-3-CARBALDEHYDE Structure

5-BROMO-2-METHO...

~%

2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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(E)-3-(5-Bromo-2-methoxy-3-pyridinyl)-1-(3,4-dichlorophenyl)-2-propen-1-one Structure

(E)-3-(5-Bromo-...

~%

2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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(E)-3-(5-bromo-2-methoxypyridin-3-yl)-1-(3,4-dichlorophenyl)prop-2-en-1-ol Structure

(E)-3-(5-bromo-...

~%

2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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1-(3,4-dichlorophenyl)ethanone Structure

1-(3,4-dichloro...

~%

2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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(E)-3-(5-Bromo-2-methoxy-3-pyridinyl)-1-(3,4-dichlorophenyl)-2-propen-1-one Structure

(E)-3-(5-Bromo-...

~%

6-bromo-2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

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2-(3,4-dichlorophenyl)-6-methylsulfanyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

~70%

2-(3,4-dichlorophenyl)-6-methylsulfonyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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5-BROMO-2-METHOXY-PYRIDINE-3-CARBALDEHYDE Structure

5-BROMO-2-METHO...

~%

2-(3,4-dichlorophenyl)-6-methylsulfonyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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5-Methanesulfonyl-1H-pyridin-2-one Structure

5-Methanesulfon...

~%

2-(3,4-dichlorophenyl)-6-methylsulfonyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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N/A Structure

~%

2-(3,4-dichlorophenyl)-6-methylsulfonyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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3-Bromo-2-methoxy-5-(methylsulfonyl)pyridine Structure

3-Bromo-2-metho...

~%

2-(3,4-dichlorophenyl)-6-methylsulfonyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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3-Iodo-5-(methylsulfonyl)-2(1H)-pyridinone Structure

3-Iodo-5-(methy...

~%

2-(3,4-dichlorophenyl)-6-methylsulfonyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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(E)-3-(5-Bromo-2-methoxy-3-pyridinyl)-1-(3,4-dichlorophenyl)-2-propen-1-one Structure

(E)-3-(5-Bromo-...

~%

2-(3,4-dichlorophenyl)-6-methylsulfonyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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(E)-3-(5-bromo-2-methoxypyridin-3-yl)-1-(3,4-dichlorophenyl)prop-2-en-1-ol Structure

(E)-3-(5-bromo-...

~%

2-(3,4-dichlorophenyl)-6-methylsulfonyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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2-Methoxy-5-(methylsulfonyl)pyridine Structure

2-Methoxy-5-(me...

~%

2-(3,4-dichlorophenyl)-6-methylsulfonyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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1-(3,4-dichlorophenyl)ethanone Structure

1-(3,4-dichloro...

~%

2-(3,4-dichlorophenyl)-6-methylsulfonyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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2-Methoxypyridine Structure

2-Methoxypyridine

~%

2-(3,4-dichlorophenyl)-6-methylsulfanyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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3,5-Dibromo-2-methoxypyridine Structure

3,5-Dibromo-2-m...

~%

2-(3,4-dichlorophenyl)-6-methylsulfanyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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6-bromo-2-(3,4-dichlorophenyl)-2H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

~%

2-(3,4-dichlorophenyl)-6-methylsulfanyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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(E)-5-Bromo-α-[2-(3,4-dichlorophenyl)ethenyl]-2-methoxy-3-pyridinemethanol Structure

(E)-5-Bromo-α-[...

~%

2-(3,4-dichlorophenyl)-6-methylsulfanyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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5-BROMO-2-METHOXY-PYRIDINE-3-CARBALDEHYDE Structure

5-BROMO-2-METHO...

~%

2-(3,4-dichlorophenyl)-6-methylsulfanyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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(E)-3-(5-Bromo-2-methoxy-3-pyridinyl)-1-(3,4-dichlorophenyl)-2-propen-1-one Structure

(E)-3-(5-Bromo-...

~%

2-(3,4-dichlorophenyl)-6-methylsulfanyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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(E)-3-(5-bromo-2-methoxypyridin-3-yl)-1-(3,4-dichlorophenyl)prop-2-en-1-ol Structure

(E)-3-(5-bromo-...

~%

2-(3,4-dichlorophenyl)-6-methylsulfanyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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1-(3,4-dichlorophenyl)ethanone Structure

1-(3,4-dichloro...

~%

2-(3,4-dichlorophenyl)-6-methylsulfanyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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2,5-Dichloropyridine Structure

2,5-Dichloropyridine

Sodium Methylate Structure

Sodium Methylate

~72%

5-Chloro-2-methoxypyridine Structure

5-Chloro-2-meth...

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2-Methoxypyridine Structure

2-Methoxypyridine

~%

6-butylsulfanyl-2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-butylsulfanyl...

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3,5-Dibromo-2-methoxypyridine Structure

3,5-Dibromo-2-m...

~%

6-butylsulfanyl-2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-butylsulfanyl...

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6-bromo-2-(3,4-dichlorophenyl)-2H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

~%

6-butylsulfanyl-2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-butylsulfanyl...

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(E)-5-Bromo-α-[2-(3,4-dichlorophenyl)ethenyl]-2-methoxy-3-pyridinemethanol Structure

(E)-5-Bromo-α-[...

~%

6-butylsulfanyl-2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-butylsulfanyl...

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5-BROMO-2-METHOXY-PYRIDINE-3-CARBALDEHYDE Structure

5-BROMO-2-METHO...

~%

6-butylsulfanyl-2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-butylsulfanyl...

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(E)-3-(5-Bromo-2-methoxy-3-pyridinyl)-1-(3,4-dichlorophenyl)-2-propen-1-one Structure

(E)-3-(5-Bromo-...

~%

6-butylsulfanyl-2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-butylsulfanyl...

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(E)-3-(5-bromo-2-methoxypyridin-3-yl)-1-(3,4-dichlorophenyl)prop-2-en-1-ol Structure

(E)-3-(5-bromo-...

~%

6-butylsulfanyl-2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-butylsulfanyl...

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1-(3,4-dichlorophenyl)ethanone Structure

1-(3,4-dichloro...

~%

6-butylsulfanyl-2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-butylsulfanyl...

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2-Methoxypyridine Structure

2-Methoxypyridine

~%

2-(3,4-dichlorophenyl)-6-methylsulfinyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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3,5-Dibromo-2-methoxypyridine Structure

3,5-Dibromo-2-m...

~%

2-(3,4-dichlorophenyl)-6-methylsulfinyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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6-bromo-2-(3,4-dichlorophenyl)-2H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

~%

2-(3,4-dichlorophenyl)-6-methylsulfinyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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(E)-5-Bromo-α-[2-(3,4-dichlorophenyl)ethenyl]-2-methoxy-3-pyridinemethanol Structure

(E)-5-Bromo-α-[...

~%

2-(3,4-dichlorophenyl)-6-methylsulfinyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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6-bromo-2-(3,4-dichlorophenyl)-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

6-bromo-2-(3,4-...

~%

2-(3,4-dichlorophenyl)-6-methylsulfinyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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5-BROMO-2-METHOXY-PYRIDINE-3-CARBALDEHYDE Structure

5-BROMO-2-METHO...

~%

2-(3,4-dichlorophenyl)-6-methylsulfinyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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(E)-3-(5-Bromo-2-methoxy-3-pyridinyl)-1-(3,4-dichlorophenyl)-2-propen-1-one Structure

(E)-3-(5-Bromo-...

~%

2-(3,4-dichlorophenyl)-6-methylsulfinyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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(E)-3-(5-bromo-2-methoxypyridin-3-yl)-1-(3,4-dichlorophenyl)prop-2-en-1-ol Structure

(E)-3-(5-bromo-...

~%

2-(3,4-dichlorophenyl)-6-methylsulfinyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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1-(3,4-dichlorophenyl)ethanone Structure

1-(3,4-dichloro...

~%

2-(3,4-dichlorophenyl)-6-methylsulfinyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine Structure

2-(3,4-dichloro...

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3, 4-Dihydro-2-phenyl-2H-pyrano [2, 3-b] pyridines with pote...

[Bargar; Dulworth; Kenny; Massad; Daniel; Wilson; Sargent Journal of Medicinal Chemistry, 1986 , vol. 29, # 9 p. 1590 - 1595]