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举例 :可输入Filippa Pettersson 或者 Cancer Res. 75(6) , 1102-12, (2015) 或者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

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

全文：HTML全文

被引用次数: 14

摘要

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-氯-2-甲氧基吡啶结构式

5-氯-2-甲氧基吡啶

~%

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

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

2-甲氧基-3-溴-5-氯吡啶结构式

2-甲氧基-3-溴-5-氯吡啶

~%

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

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

未登录结构式

~%

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

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

2,5-二氯吡啶结构式

2,5-二氯吡啶

~%

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

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

5-氯-2-甲氧基吡啶结构式

5-氯-2-甲氧基吡啶

~%

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

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

2-甲氧基-3-溴-5-氯吡啶结构式

2-甲氧基-3-溴-5-氯吡啶

~%

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

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

2,5-二氯吡啶结构式

2,5-二氯吡啶

~%

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

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

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

(E)-5-Bromo-α-[...

~86%

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

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

2-甲氧基吡啶结构式

2-甲氧基吡啶

~%

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

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

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

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

~%

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

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

5-溴-2-甲氧基吡啶-3-甲醛结构式

5-溴-2-甲氧基吡啶-3-甲醛

~%

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

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

3,4-二氯苯乙酮结构式

3,4-二氯苯乙酮

~%

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

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

2-甲氧基-3,5-二溴吡啶结构式

2-甲氧基-3,5-二溴吡啶

N,N-二甲基甲酰胺结构式

N,N-二甲基甲酰胺

~%

5-溴-6-甲氧基烟醛结构式

5-溴-6-甲氧基烟醛

5-溴-2-甲氧基吡啶-3-甲醛结构式

5-溴-2-甲氧基吡啶-3-甲醛

2-甲氧基-3-溴-5-氯吡啶结构式

2-甲氧基-3-溴-5-氯吡啶

N,N-二甲基甲酰胺结构式

N,N-二甲基甲酰胺

~%

5-溴-6-甲氧基烟醛结构式

5-溴-6-甲氧基烟醛

5-氯-2-甲氧基烟醛结构式

5-氯-2-甲氧基烟醛

2-甲氧基-3,5-二溴吡啶结构式

2-甲氧基-3,5-二溴吡啶

~%

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

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

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

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

~79%

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

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

2-甲氧基吡啶结构式

2-甲氧基吡啶

~%

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

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

2-甲氧基-3,5-二溴吡啶结构式

2-甲氧基-3,5-二溴吡啶

~%

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

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

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

(E)-5-Bromo-α-[...

~%

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

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

5-溴-2-甲氧基吡啶-3-甲醛结构式

5-溴-2-甲氧基吡啶-3-甲醛

~%

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

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

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

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

~%

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

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

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

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

~%

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

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

3,4-二氯苯乙酮结构式

3,4-二氯苯乙酮

~%

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

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

2-甲氧基吡啶结构式

2-甲氧基吡啶

~0%

5-溴-2-甲氧基吡啶结构式

5-溴-2-甲氧基吡啶

2-甲氧基-3,5-二溴吡啶结构式

2-甲氧基-3,5-二溴吡啶

2-甲氧基吡啶结构式

2-甲氧基吡啶

~70%

5-溴-2-甲氧基吡啶结构式

5-溴-2-甲氧基吡啶

2-甲氧基-3,5-二溴吡啶结构式

2-甲氧基-3,5-二溴吡啶

5-氯-2-甲氧基吡啶结构式

5-氯-2-甲氧基吡啶

~%

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

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

2-甲氧基-3-溴-5-氯吡啶结构式

2-甲氧基-3-溴-5-氯吡啶

~%

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

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

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

(E)-5-Chloro-α-...

~%

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

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

2,5-二氯吡啶结构式

2,5-二氯吡啶

~%

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

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

2-甲氧基吡啶结构式

2-甲氧基吡啶

~%

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

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

2-甲氧基-3,5-二溴吡啶结构式

2-甲氧基-3,5-二溴吡啶

~%

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

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

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

(E)-5-Bromo-α-[...

~%

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

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

5-溴-2-甲氧基吡啶-3-甲醛结构式

5-溴-2-甲氧基吡啶-3-甲醛

~%

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

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

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

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

~%

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

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

3,4-二氯苯乙酮结构式

3,4-二氯苯乙酮

~%

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

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

2-甲氧基吡啶结构式

2-甲氧基吡啶

~%

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

2-(3,4-dichloro...

2-甲氧基-3,5-二溴吡啶结构式

2-甲氧基-3,5-二溴吡啶

~%

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

2-(3,4-dichloro...

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

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

~%

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

2-(3,4-dichloro...

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

(E)-5-Bromo-α-[...

~%

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

2-(3,4-dichloro...

5-溴-2-甲氧基吡啶-3-甲醛结构式

5-溴-2-甲氧基吡啶-3-甲醛

~%

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

2-(3,4-dichloro...

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

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

~%

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

2-(3,4-dichloro...

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

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

~%

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

2-(3,4-dichloro...

3,4-二氯苯乙酮结构式

3,4-二氯苯乙酮

~%

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

2-(3,4-dichloro...

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

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

~%

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

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

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

2-(3,4-dichloro...

~70%

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

2-(3,4-dichloro...

5-溴-2-甲氧基吡啶-3-甲醛结构式

5-溴-2-甲氧基吡啶-3-甲醛

~%

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

2-(3,4-dichloro...

5-Methanesulfonyl-1H-pyridin-2-one结构式

5-Methanesulfon...

~%

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

2-(3,4-dichloro...

未登录结构式

~%

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

2-(3,4-dichloro...

3-Bromo-2-methoxy-5-(methylsulfonyl)pyridine结构式

3-Bromo-2-metho...

~%

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

2-(3,4-dichloro...

3-Iodo-5-(methylsulfonyl)-2(1H)-pyridinone结构式

3-Iodo-5-(methy...

~%

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

2-(3,4-dichloro...

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

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

~%

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

2-(3,4-dichloro...

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

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

~%

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

2-(3,4-dichloro...

2-Methoxy-5-(methylsulfonyl)pyridine结构式

2-Methoxy-5-(me...

~%

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

2-(3,4-dichloro...

3,4-二氯苯乙酮结构式

3,4-二氯苯乙酮

~%

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

2-(3,4-dichloro...

2-甲氧基吡啶结构式

2-甲氧基吡啶

~%

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

2-(3,4-dichloro...

2-甲氧基-3,5-二溴吡啶结构式

2-甲氧基-3,5-二溴吡啶

~%

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

2-(3,4-dichloro...

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

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

~%

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

2-(3,4-dichloro...

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

(E)-5-Bromo-α-[...

~%

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

2-(3,4-dichloro...

5-溴-2-甲氧基吡啶-3-甲醛结构式

5-溴-2-甲氧基吡啶-3-甲醛

~%

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

2-(3,4-dichloro...

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

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

~%

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

2-(3,4-dichloro...

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

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

~%

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

2-(3,4-dichloro...

3,4-二氯苯乙酮结构式

3,4-二氯苯乙酮

~%

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

2-(3,4-dichloro...

2,5-二氯吡啶结构式

2,5-二氯吡啶

甲醇钠结构式

~72%

5-氯-2-甲氧基吡啶结构式

5-氯-2-甲氧基吡啶

2-甲氧基吡啶结构式

2-甲氧基吡啶

~%

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

6-butylsulfanyl...

2-甲氧基-3,5-二溴吡啶结构式

2-甲氧基-3,5-二溴吡啶

~%

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

6-butylsulfanyl...

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

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

~%

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

6-butylsulfanyl...

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

(E)-5-Bromo-α-[...

~%

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

6-butylsulfanyl...

5-溴-2-甲氧基吡啶-3-甲醛结构式

5-溴-2-甲氧基吡啶-3-甲醛

~%

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

6-butylsulfanyl...

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

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

~%

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

6-butylsulfanyl...

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

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

~%

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

6-butylsulfanyl...

3,4-二氯苯乙酮结构式

3,4-二氯苯乙酮

~%

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

6-butylsulfanyl...

2-甲氧基吡啶结构式

2-甲氧基吡啶

~%

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

2-(3,4-dichloro...

2-甲氧基-3,5-二溴吡啶结构式

2-甲氧基-3,5-二溴吡啶

~%

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

2-(3,4-dichloro...

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

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

~%

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

2-(3,4-dichloro...

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

(E)-5-Bromo-α-[...

~%

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

2-(3,4-dichloro...

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

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

~%

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

2-(3,4-dichloro...

5-溴-2-甲氧基吡啶-3-甲醛结构式

5-溴-2-甲氧基吡啶-3-甲醛

~%

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

2-(3,4-dichloro...

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

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

~%

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

2-(3,4-dichloro...

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

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

~%

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

2-(3,4-dichloro...

3,4-二氯苯乙酮结构式

3,4-二氯苯乙酮

~%

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

2-(3,4-dichloro...

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]