Tetrahedron

Synthesis of 1, 2-benzisothiazolin-3-ones by ring transformation of 1, 3-benzoxathiin-4-one 1-oxides

…, T Shimazaki, T Yoshida, W Ando, T Konakahara

Index: Shimizu, Masao; Shimazaki, Teruaki; Yoshida, Tetsuya; Ando, Wataru; Konakahara, Takeo Tetrahedron, 2012 , vol. 68, # 21 p. 3932 - 3936

Full Text: HTML

Citation Number: 2

Abstract

1, 2-Benzisothiazolin-3-ones were synthesized from 1, 3-benzoxathiin-4-one 1-oxides by means of a nonhazardous and inexpensive method. The 1, 3-benzoxathiin-4-one 1-oxides were prepared by oxidation of 1, 3-benzoxathiin-4-ones with hydrogen peroxide in the presence of a catalyst. Attack of amines on the carbonyl groups of the 1, 3-benzoxathiin-4- one 1-oxides and subsequent elimination of carbonyl compounds likely produced sulfenic ...

 Related Synthetic Route
N/A Structure

1236311-86-6

N/A

p-Anisidine Structure

104-94-9

p-Anisidine

~75%

2-(4-Methoxyphenyl)-1,2-benzothiazol-3(2H)-one Structure

2514-33-2

2-(4-Methoxyphe...

2-ethylbenzo[d]-1,3-oxathiin-4-one Structure

38057-98-6

2-ethylbenzo[d]...

~%

2-(4-Methoxyphenyl)-1,2-benzothiazol-3(2H)-one Structure

2514-33-2

2-(4-Methoxyphe...

N/A Structure

1236311-86-6

N/A

Structure

74497-02-2

~77%

2-phenyl-1,2-benzisothiazol-3-(2H)-one Structure

2527-03-9

2-phenyl-1,2-be...

N/A Structure

1236311-86-6

N/A

2-Aminoethanol Structure

141-43-5

2-Aminoethanol

~70%

2-(2-hydroxyethyl)-1,2-benzothiazol-3-one Structure

4299-09-6

2-(2-hydroxyeth...

2-ethylbenzo[d]-1,3-oxathiin-4-one Structure

38057-98-6

2-ethylbenzo[d]...

~%

2-(2-hydroxyethyl)-1,2-benzothiazol-3-one Structure

4299-09-6

2-(2-hydroxyeth...

2-phenylbenzo[d]-1,3-oxathiin-4-one 1-oxide Structure

86212-65-9

2-phenylbenzo[d...

n-butylamine Structure

109-73-9

n-butylamine

~81%

2-Butyl-1,2-benzisothiazolin-3-one Structure

4299-07-4

2-Butyl-1,2-ben...

N/A Structure

1236311-86-6

N/A

n-butylamine Structure

109-73-9

n-butylamine

~89%

2-Butyl-1,2-benzisothiazolin-3-one Structure

4299-07-4

2-Butyl-1,2-ben...

2-phenylbenzo[d]-1,3-oxathiin-4-one 1-oxide Structure

86212-65-9

2-phenylbenzo[d...

Benzylamine Structure

100-46-9

Benzylamine

~95%

2-benzyl-1,2-benzothiazol-3-one Structure

2514-36-5

2-benzyl-1,2-be...

N/A Structure

1236311-88-8

N/A

Benzylamine Structure

100-46-9

Benzylamine

~81%

2-benzyl-1,2-benzothiazol-3-one Structure

2514-36-5

2-benzyl-1,2-be...

N/A Structure

36665-23-3

N/A

Benzylamine Structure

100-46-9

Benzylamine

~89%

2-benzyl-1,2-benzothiazol-3-one Structure

2514-36-5

2-benzyl-1,2-be...

N/A Structure

1236311-86-6

N/A

Benzylamine Structure

100-46-9

Benzylamine

~93%

2-benzyl-1,2-benzothiazol-3-one Structure

2514-36-5

2-benzyl-1,2-be...

4H-3,1-Benzoxathiin-4-one,2-(1-methylethyl)- Structure

94442-82-7

4H-3,1-Benzoxat...

~%

2-benzyl-1,2-benzothiazol-3-one Structure

2514-36-5

2-benzyl-1,2-be...

8-oxa-10-thiabicyclo[4.4.0]deca-1,3,5-trien-7-one Structure

5651-33-2

8-oxa-10-thiabi...

~%

2-benzyl-1,2-benzothiazol-3-one Structure

2514-36-5

2-benzyl-1,2-be...

2-ethylbenzo[d]-1,3-oxathiin-4-one Structure

38057-98-6

2-ethylbenzo[d]...

~%

2-benzyl-1,2-benzothiazol-3-one Structure

2514-36-5

2-benzyl-1,2-be...

4H-3,1-Benzoxathiin-4-one,2-phenyl- Structure

5651-35-4

4H-3,1-Benzoxat...

~%

2-benzyl-1,2-benzothiazol-3-one Structure

2514-36-5

2-benzyl-1,2-be...

N/A Structure

1236311-86-6

N/A

~41%

Benzisothiazolone Structure

2634-33-5

Benzisothiazolone

2-ethylbenzo[d]-1,3-oxathiin-4-one Structure

38057-98-6

2-ethylbenzo[d]...

~%

Benzisothiazolone Structure

2634-33-5

Benzisothiazolone

N/A Structure

1236311-86-6

N/A

p-Toluidine Structure

106-49-0

p-Toluidine

~77%

PBIT Structure

2514-30-9

PBIT

2-ethylbenzo[d]-1,3-oxathiin-4-one Structure

38057-98-6

2-ethylbenzo[d]...

~%

PBIT Structure

2514-30-9

PBIT


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