The Journal of Organic Chemistry

Photochemical and thermal reactions of aromatic Schiff bases

E Tauer, KH Grellmann

Index: Tauer, Erich; Grellmann, Karl H. Journal of Organic Chemistry, 1981 , vol. 46, # 21 p. 4252 - 4258

Full Text: HTML

Citation Number: 39

Abstract

The photochemical and thermal reactions of aromatic Schiff bases (SB) prepared from o- aminophenol and aldehydes and from 0-aminophenol and ketones are compared. All SBs are converted by light into the corresponding benzoxazoliies. For the SBs derived from aldehydes, benzoxazoline formation is a prerequisite to convert them by a second photon into benzoxazoles. In some cases oxygen is not required for this second reaction step. ...

 Related Synthetic Route
2-Phenyl-3-acetylbenzoxazoline Structure

78685-72-0

2-Phenyl-3-acet...

~69%

2-Phenylbenzoxazole Structure

833-50-1

2-Phenylbenzoxazole

Furfural Structure

98-01-1

Furfural

~%

2-(FURAN-2-YL)BENZO[D]OXAZOLE Structure

881-60-7

2-(FURAN-2-YL)B...

aminophenol Structure

95-55-6

aminophenol

~%

2-(FURAN-2-YL)BENZO[D]OXAZOLE Structure

881-60-7

2-(FURAN-2-YL)B...

aminophenol Structure

95-55-6

aminophenol

~%

2-(2-methoxyphenyl)-1,3-benzoxazole Structure

13459-17-1

2-(2-methoxyphe...

o-Anisaldehyde Structure

135-02-4

o-Anisaldehyde

~%

2-(2-methoxyphenyl)-1,3-benzoxazole Structure

13459-17-1

2-(2-methoxyphe...

trans-N-(3-Phenyl-2-propenylidene)-o-aminophenol Structure

694472-13-4

trans-N-(3-Phen...

~%

(E)-2-DEOXY-2-(FLUOROMETHYLENE)CYTIDINE Structure

78685-70-8

(E)-2-DEOXY-2-(...

Cinnamaldehyde Structure

104-55-2

Cinnamaldehyde

~%

(E)-2-DEOXY-2-(FLUOROMETHYLENE)CYTIDINE Structure

78685-70-8

(E)-2-DEOXY-2-(...

aminophenol Structure

95-55-6

aminophenol

~%

(E)-2-DEOXY-2-(FLUOROMETHYLENE)CYTIDINE Structure

78685-70-8

(E)-2-DEOXY-2-(...

2-styryl-2,3-dihydrobenzo[d]oxazole Structure

717882-18-3

2-styryl-2,3-di...

~%

(E)-2-DEOXY-2-(FLUOROMETHYLENE)CYTIDINE Structure

78685-70-8

(E)-2-DEOXY-2-(...

2-styryl-2,3-dihydrobenzo[d]oxazole Structure

717882-18-3

2-styryl-2,3-di...

~%

(E)-2-DEOXY-2-(FLUOROMETHYLENE)CYTIDINE Structure

78685-70-8

(E)-2-DEOXY-2-(...

(E)-2-(2-phenylethenyl)-benzoxazole Structure

59066-62-5

(E)-2-(2-phenyl...

(E)-2-(2-phenylethenyl)-benzoxazole Structure

59066-62-5

(E)-2-(2-phenyl...

~30%

(E)-2-DEOXY-2-(FLUOROMETHYLENE)CYTIDINE Structure

78685-70-8

(E)-2-DEOXY-2-(...

N-(1-o-Tolylpropylidene)-o-aminophenol Structure

78685-82-2

N-(1-o-Tolylpro...

~20%

2-(2-methylphenyl)-1,3-benzoxazole Structure

32959-60-7

2-(2-methylphen...

2'-Methylpropiophenone Structure

2040-14-4

2'-Methylpropio...

~%

2-(2-methylphenyl)-1,3-benzoxazole Structure

32959-60-7

2-(2-methylphen...

aminophenol Structure

95-55-6

aminophenol

~%

2-(2-methylphenyl)-1,3-benzoxazole Structure

32959-60-7

2-(2-methylphen...

2-Methyl-3-o-tolyl-2H-1,4-benzoxazin-2-ol Structure

78685-83-3

2-Methyl-3-o-to...

~%

2-(2-methylphenyl)-1,3-benzoxazole Structure

32959-60-7

2-(2-methylphen...

4-hydroxybenzaldehyde Structure

123-08-0

4-hydroxybenzal...

~%

4-(BENZO[D]OXAZOL-2-YL)PHENOL Structure

3315-19-3

4-(BENZO[D]OXAZ...

Phenol,2-[[(4-hydroxyphenyl)methylene]amino]- Structure

17065-03-1

Phenol,2-[[(4-h...

~%

4-(BENZO[D]OXAZOL-2-YL)PHENOL Structure

3315-19-3

4-(BENZO[D]OXAZ...

aminophenol Structure

95-55-6

aminophenol

~%

4-(BENZO[D]OXAZOL-2-YL)PHENOL Structure

3315-19-3

4-(BENZO[D]OXAZ...

2-(4-methoxyphenyl)-2,3-dihydrobenzo[d]oxazole Structure

673435-36-4

2-(4-methoxyphe...

~45%

2-(4-methoxyphenyl)-1,3-benzoxazole Structure

838-34-6

2-(4-methoxyphe...

Phenol,2-[[(4-methoxyphenyl)methylene]amino]- Structure

3117-67-7

Phenol,2-[[(4-m...

~%

2-(4-methoxyphenyl)-1,3-benzoxazole Structure

838-34-6

2-(4-methoxyphe...

Phenol,2-[[(4-methoxyphenyl)methylene]amino]- Structure

3117-67-7

Phenol,2-[[(4-m...

2-(4-methoxyphenyl)-2,3-dihydrobenzo[d]oxazole Structure

673435-36-4

2-(4-methoxyphe...


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