3, 4-Dihydro-2-phenyl-2H-pyrano [2, 3-b] pyridines with potent antirhinovirus activity

…, JK Dulworth, MT Kenny, R Massad…

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

Full Text: HTML

Citation Number: 17

Abstract

Chemistry. The general synthesis route for the title compounds is outlined in Scheme I. Bromination of 5-chloro-2-methoxypyridine produced the 3-bromo derivative 2a. Similarly, bromination of 2-methoxypyridine with an extra equivalent of bromine gave the dibromopyridine 2b. Bromine-lithium exchange was effected with n-butyllithium in ether at- 70" C, and the intermediate lithiopyridines were trapped with the appropriate cinnam- ...

 Related Synthetic Route
N/A Structure

102830-83-1

N/A

~54%

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

102830-65-9

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

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

102830-76-2

(E)-5-Chloro-α-...

~82%

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

102830-80-8

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

2-Methoxypyridine Structure

1628-89-3

2-Methoxypyridine

~71%

3,5-Dibromo-2-methoxypyridine Structure

13472-60-1

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

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

102830-64-8

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

~82%

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

102830-84-2

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

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

102830-80-8

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

~65%

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

102830-62-6

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

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

102830-82-0

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

~59%

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

102830-64-8

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

2-Methoxypyridine Structure

1628-89-3

2-Methoxypyridine

~%

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

102830-69-3

2-(3,4-dichloro...

3,5-Dibromo-2-methoxypyridine Structure

13472-60-1

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

~%

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

102830-69-3

2-(3,4-dichloro...

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

102830-82-0

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

~%

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

102830-69-3

2-(3,4-dichloro...

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

102830-78-4

(E)-5-Bromo-α-[...

~%

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

102830-69-3

2-(3,4-dichloro...

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

102830-64-8

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

~%

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

102830-69-3

2-(3,4-dichloro...

5,6-Dithiadecane Structure

629-45-8

5,6-Dithiadecane

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

102830-64-8

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

~%

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

102830-73-9

6-butylsulfanyl...

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

102830-74-0

2-(3,4-dichloro...

~63%

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

102830-70-6

2-(3,4-dichloro...


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