e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

3??Oxo??1, 2??benzoisothiazoline??2??acetic acid 1, 1??dioxide derivatives. I. Reaction of esters with alkoxides

CB Schapira, IA Perillo…

Index: Schapira, Celia B.; Perillo, Isabel A.; Lamdan, Samuel Journal of Heterocyclic Chemistry, 1980 , vol. 17, p. 1281 - 1288

Full Text: HTML

Citation Number: 21

Abstract

Abstract Reaction of 3-oxo-1, 2-benzoisothiazoline-2-acetic acid alkyl esters 1, 1-dioxide (1a- d) with alkaline alkoxides was carried out under various conditions. Under mild conditions, o- (N-carboxymethylsulfamyl) benzoic acids dialkyl esters (2a-d) were obtained with good yields. Reaction of 1a-d or 2a-d with sodium alkoxides under drastic conditions afforded 4- hydroxy-2H-1, 2-benzothiazine-3-carboxylic acid alkyl esters 1, 1-dioxide (3a-d). ...

Isopropyl chloroacetate Structure

Isopropyl chlor...

Sodium Saccharin Structure

Sodium Saccharin

~73%

propan-2-yl 2-(1,1,3-trioxo-1,2-benzothiazol-2-yl)acetate Structure

propan-2-yl 2-(...

methyl 2-(1,1,3-trioxo-1,2-benzothiazol-2-yl)acetate Structure

methyl 2-(1,1,3...

Sodium ethoxide Structure

Sodium ethoxide

~75%

Methyl 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide Structure

Methyl 4-Hydrox...

Ethyl 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide Structure

Ethyl 4-Hydroxy...

2-((TERT-BUTYLDIMETHYLSILYLOXY)METHYL)-6-((TRIMETHYLSILYL)ETHYNYL)FURO[3,2-B]PYRIDINE Structure

2-((TERT-BUTYLD...

Sodium ethoxide Structure

Sodium ethoxide

~60%

Ethyl 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide Structure

Ethyl 4-Hydroxy...

Sodium ethoxide Structure

Sodium ethoxide

ethyl 2-(N-(2-ethoxy-2-oxoethyl)sulfamoyl)benzoate Structure

ethyl 2-(N-(2-e...

~%

Ethyl 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide Structure

Ethyl 4-Hydroxy...

methyl 2-(1,1,3-trioxo-1,2-benzothiazol-2-yl)acetate Structure

methyl 2-(1,1,3...

~%

4-methyl-1-naphthalen-1-ylsulfonylpiperidine Structure

4-methyl-1-naph...

Sodium Saccharin Structure

Sodium Saccharin

~%

4-methyl-1-naphthalen-1-ylsulfonylpiperidine Structure

4-methyl-1-naph...

(1,1,3-trioxo-1,3-dihydro-1λ6-benzo[d]isothiazol-2-yl)-acetic acid tert-butyl ester Structure

(1,1,3-trioxo-1...

~%

4-methyl-1-naphthalen-1-ylsulfonylpiperidine Structure

4-methyl-1-naph...

2-((TERT-BUTYLDIMETHYLSILYLOXY)METHYL)-6-((TRIMETHYLSILYL)ETHYNYL)FURO[3,2-B]PYRIDINE Structure

2-((TERT-BUTYLD...

~%

4-methyl-1-naphthalen-1-ylsulfonylpiperidine Structure

4-methyl-1-naph...

propan-2-yl 2-(1,1,3-trioxo-1,2-benzothiazol-2-yl)acetate Structure

propan-2-yl 2-(...

~%

4-methyl-1-naphthalen-1-ylsulfonylpiperidine Structure

4-methyl-1-naph...

methyl 2-[(2-methoxy-2-oxoethyl)sulfamoyl]benzoate Structure

methyl 2-[(2-me...

~%

4-methyl-1-naphthalen-1-ylsulfonylpiperidine Structure

4-methyl-1-naph...

phenyl 2-(1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)acetate Structure

phenyl 2-(1,1-d...

~%

4-methyl-1-naphthalen-1-ylsulfonylpiperidine Structure

4-methyl-1-naph...

propan-2-yl 4-hydroxy-1,1-dioxo-2H-1λ6,2-benzothiazine-3-carboxylate Structure

propan-2-yl 4-h...

~%

4-methyl-1-naphthalen-1-ylsulfonylpiperidine Structure

4-methyl-1-naph...

ethyl 2-(N-(2-ethoxy-2-oxoethyl)sulfamoyl)benzoate Structure

ethyl 2-(N-(2-e...

~%

4-methyl-1-naphthalen-1-ylsulfonylpiperidine Structure

4-methyl-1-naph...

isopropyl 2-(N-(2-isopropoxy-2-oxoethyl)sulfamoyl)benzoate Structure

isopropyl 2-(N-...

~%

4-methyl-1-naphthalen-1-ylsulfonylpiperidine Structure

4-methyl-1-naph...

2H-1,2-benzothiazin-4(3H)one-3-carboxylic acid 1,1-dioxide Structure

2H-1,2-benzothi...

~%

4-methyl-1-naphthalen-1-ylsulfonylpiperidine Structure

4-methyl-1-naph...

Ethyl 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide Structure

Ethyl 4-Hydroxy...

~%

4-methyl-1-naphthalen-1-ylsulfonylpiperidine Structure

4-methyl-1-naph...

(1,1,3-trioxo-1,3-dihydro-1λ6-benzo[d]isothiazol-2-yl)-acetic acid tert-butyl ester Structure

(1,1,3-trioxo-1...

Sodium Methylate Structure

Sodium Methylate

~77%

Methyl 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide Structure

Methyl 4-Hydrox...

2-((TERT-BUTYLDIMETHYLSILYLOXY)METHYL)-6-((TRIMETHYLSILYL)ETHYNYL)FURO[3,2-B]PYRIDINE Structure

2-((TERT-BUTYLD...

Sodium Methylate Structure

Sodium Methylate

~76%

Methyl 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide Structure

Methyl 4-Hydrox...

Sodium Methylate Structure

Sodium Methylate

propan-2-yl 2-(1,1,3-trioxo-1,2-benzothiazol-2-yl)acetate Structure

propan-2-yl 2-(...

~76%

Methyl 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide Structure

Methyl 4-Hydrox...

Sodium Methylate Structure

Sodium Methylate

phenyl 2-(1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)acetate Structure

phenyl 2-(1,1-d...

~82%

Methyl 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide Structure

Methyl 4-Hydrox...

methyl 2-(1,1,3-trioxo-1,2-benzothiazol-2-yl)acetate Structure

methyl 2-(1,1,3...

Sodium Methylate Structure

Sodium Methylate

~70%

Methyl 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide Structure

Methyl 4-Hydrox...

methyl 2-(1,1,3-trioxo-1,2-benzothiazol-2-yl)acetate Structure

methyl 2-(1,1,3...

Sodium Methylate Structure

Sodium Methylate

~0%

methyl 2-[(2-methoxy-2-oxoethyl)sulfamoyl]benzoate Structure

methyl 2-[(2-me...

Methyl 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide Structure

Methyl 4-Hydrox...

Detail

(1,1,3-trioxo-1,3-dihydro-1λ6-benzo[d]isothiazol-2-yl)-acetic acid tert-butyl ester Structure

(1,1,3-trioxo-1...

Sodium Methylate Structure

Sodium Methylate

~68%

methyl 2-[(2-methoxy-2-oxoethyl)sulfamoyl]benzoate Structure

methyl 2-[(2-me...

methyl 2-(1,1,3-trioxo-1,2-benzothiazol-2-yl)acetate Structure

methyl 2-(1,1,3...

Sodium Methylate Structure

Sodium Methylate

~0%

methyl 2-[(2-methoxy-2-oxoethyl)sulfamoyl]benzoate Structure

methyl 2-[(2-me...

Methyl 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide Structure

Methyl 4-Hydrox...

Detail