Synthesis of Substituted Pyridines by a Cycloaddition Route Using Nitrile Oxides and Homoallyl Alcohols

S Kanemasa, Y Asai, J Tanaka

Index: Kanemasa Asai; Tanaka Bulletin of the Chemical Society of Japan, 1991 , vol. 64, # 2 p. 375 - 380

Full Text: HTML

Citation Number: 12

Abstract

Cycloadditions of nitrile oxides with unprotected homoallyl alcohols, followed by Swern oxidations, lead to 5-(2-oxoalkyl)-2-isoxazolines. Subsequent Raney Ni reduction of the resulting heterocycles in ethanol in the presence of excess tetrafluoroboric acid affords substituted pyridine derivatives.

 Related Synthetic Route
N/A Structure

134370-17-5

N/A

~53%

3-methyl-2,6-diphenylpyridine Structure

28489-52-3

3-methyl-2,6-di...

2-Methyl-1-phenyl-3-buten-1-ol Structure

25201-44-9

2-Methyl-1-phen...

~%

3-methyl-2,6-diphenylpyridine Structure

28489-52-3

3-methyl-2,6-di...

1-phenyl-2-(3-phenyl-4,5-dihydroisoxazol-5-yl)propan-1-ol Structure

134370-19-7

1-phenyl-2-(3-p...

~%

3-methyl-2,6-diphenylpyridine Structure

28489-52-3

3-methyl-2,6-di...

Alpha-Chlorobenzaldoxime Structure

698-16-8

Alpha-Chloroben...

~%

3-methyl-2,6-diphenylpyridine Structure

28489-52-3

3-methyl-2,6-di...

5-(2-Oxo-2-phenylethyl)-3-methyl-2-isoxazoline Structure

134370-38-0

5-(2-Oxo-2-phen...

~49%

2-METHYL-6-PHENYLPYRIDINE Structure

46181-30-0

2-METHYL-6-PHEN...

1-phenyl-3-buten-1-ol Structure

80735-94-0

1-phenyl-3-bute...

~%

2-METHYL-6-PHENYLPYRIDINE Structure

46181-30-0

2-METHYL-6-PHEN...

2-(3-methyl-4,5-dihydroisoxazol-5-yl)-1-phenylethanol Structure

134370-26-6

2-(3-methyl-4,5...

~%

2-METHYL-6-PHENYLPYRIDINE Structure

46181-30-0

2-METHYL-6-PHEN...

5-(2-Oxobutyl)-3-methyl-2-isoxazoline Structure

134370-39-1

5-(2-Oxobutyl)-...

~39%

2-ETHYL-6-METHYLPYRIDINE Structure

1122-69-6

2-ETHYL-6-METHY...

5-(2-Oxo-2-phenylethyl)-3-phenyl-2-isoxazoline Structure

82552-42-9

5-(2-Oxo-2-phen...

~81%

2,6-DIPHENYLPYRIDINE Structure

3558-69-8

2,6-DIPHENYLPYRIDINE

2-(5-methyl-3-phenyl-4,5-dihydroisoxazol-5-yl)-1-phenylethanone Structure

134370-29-9

2-(5-methyl-3-p...

~96%

4-methyl-2,6-diphenylpyridine Structure

53531-57-0

4-methyl-2,6-di...

3-Methyl-1-phenyl-3-buten-1-ol Structure

23092-23-1

3-Methyl-1-phen...

~%

4-methyl-2,6-diphenylpyridine Structure

53531-57-0

4-methyl-2,6-di...

2-(5-methyl-3-phenyl-4,5-dihydroisoxazol-5-yl)-1-phenylethanol Structure

134370-18-6

2-(5-methyl-3-p...

~%

4-methyl-2,6-diphenylpyridine Structure

53531-57-0

4-methyl-2,6-di...

Alpha-Chlorobenzaldoxime Structure

698-16-8

Alpha-Chloroben...

~%

4-methyl-2,6-diphenylpyridine Structure

53531-57-0

4-methyl-2,6-di...

5-[2-Oxo-2-(2-pyridyl)ethyl]-3-phenyl-2-isoxazoline Structure

134370-32-4

5-[2-Oxo-2-(2-p...

~12%

6-Phenyl-2,2'-bipyridine Structure

61633-06-5

6-Phenyl-2,2'-b...

(RS)-1-(2-pyridyl)but-3-en-1-ol Structure

17285-57-3

(RS)-1-(2-pyrid...

~%

6-Phenyl-2,2'-bipyridine Structure

61633-06-5

6-Phenyl-2,2'-b...

N/A Structure

134370-20-0

N/A

~%

6-Phenyl-2,2'-bipyridine Structure

61633-06-5

6-Phenyl-2,2'-b...

Alpha-Chlorobenzaldoxime Structure

698-16-8

Alpha-Chloroben...

~%

6-Phenyl-2,2'-bipyridine Structure

61633-06-5

6-Phenyl-2,2'-b...

Ethyl 5-(2-Oxobutyl)-2-isoxazoline-3-carboxylate Structure

134370-37-9

Ethyl 5-(2-Oxob...

~60%

Ethyl 6-ethylpicolinate Structure

41337-78-4

Ethyl 6-ethylpi...

5-(2-Oxo-2-phenylethyl)-3-(4-methoxyphenyl)-2-isoxazoline Structure

134370-34-6

5-(2-Oxo-2-phen...

~58%

2-(4-methoxyphenyl)-6-phenyl-pyridine Structure

33777-95-6

2-(4-methoxyphe...

1-phenyl-3-buten-1-ol Structure

80735-94-0

1-phenyl-3-bute...

~%

2-(4-methoxyphenyl)-6-phenyl-pyridine Structure

33777-95-6

2-(4-methoxyphe...

2-(3-(4-methoxyphenyl)-4,5-dihydroisoxazol-5-yl)-1-phenylethan-1-ol Structure

724454-75-5

2-(3-(4-methoxy...

~%

2-(4-methoxyphenyl)-6-phenyl-pyridine Structure

33777-95-6

2-(4-methoxyphe...

N-HYDROXY-4-METHOXYBENZENECARBOXIMIDOYL CHLORIDE Structure

38435-51-7

N-HYDROXY-4-MET...

~%

2-(4-methoxyphenyl)-6-phenyl-pyridine Structure

33777-95-6

2-(4-methoxyphe...

5-(2-Oxobutyl)-3-phenyl-2-isoxazoline Structure

134370-31-3

5-(2-Oxobutyl)-...

~50%

2-Ethyl-6-phenylpyridine Structure

59239-12-2

2-Ethyl-6-pheny...

hex-5-en-3-ol Structure

688-99-3

hex-5-en-3-ol

~%

2-Ethyl-6-phenylpyridine Structure

59239-12-2

2-Ethyl-6-pheny...

N/A Structure

134370-45-9

N/A

~%

2-Ethyl-6-phenylpyridine Structure

59239-12-2

2-Ethyl-6-pheny...

Alpha-Chlorobenzaldoxime Structure

698-16-8

Alpha-Chloroben...

~%

2-Ethyl-6-phenylpyridine Structure

59239-12-2

2-Ethyl-6-pheny...


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