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

Tetrahedron

Reactions of o-aminothiophenol withαβ-unsaturated dicarbonyl systems. Facile synthesis of benzothiazines and benzothiazepines

V Balasubramaniyan, P Balasubramaniyan, AS Shaikh

Index: Balasubramaniyan, V.; Balasubramaniyan, P.; Shaikh, A. S. Tetrahedron, 1986 , vol. 42, # 10 p. 2731 - 2738

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Citation Number: 22

Abstract

When treated with maleanilic/fumaranilic acids or esters or the corresponding imides or isoimides, o-aminothiophenol furnishes benzothiazines, whereas treatment of o- aminothiophenol with acrylic acids/esters furnishes benzothiazepines. The orientational preferences in these Michael-type reactions are discussed.

2-Butenoic acid,4-oxo-4-(phenylamino)-, (2Z)- Structure

2-Butenoic acid...

2-Aminothiophenol Structure

2-Aminothiophenol

~79%

2-(3-oxo-4H-1,4-benzothiazin-2-yl)-N-phenylacetamide Structure

2-(3-oxo-4H-1,4...

N-Phenylisomaleimide Structure

N-Phenylisomaleimide

2-Aminothiophenol Structure

2-Aminothiophenol

~%

2-(3-oxo-4H-1,4-benzothiazin-2-yl)-N-phenylacetamide Structure

2-(3-oxo-4H-1,4...

N-Phenylmaleimide Structure

N-Phenylmaleimide

2-Aminothiophenol Structure

2-Aminothiophenol

~%

2-(3-oxo-4H-1,4-benzothiazin-2-yl)-N-phenylacetamide Structure

2-(3-oxo-4H-1,4...

2-Butenoic acid,4-[(3-chlorophenyl)amino]-4-oxo-, (2Z)- Structure

2-Butenoic acid...

2-Aminothiophenol Structure

2-Aminothiophenol

~91%

2-[4-(3-chlorophenyl)-3-oxo-1,4-benzothiazin-2-yl]acetamide Structure

2-[4-(3-chlorop...

methyl (Z)-4-((3-chlorophenyl)amino)-4-oxobut-2-enoate Structure

methyl (Z)-4-((...

2-Aminothiophenol Structure

2-Aminothiophenol

~94%

2-[4-(3-chlorophenyl)-3-oxo-1,4-benzothiazin-2-yl]acetamide Structure

2-[4-(3-chlorop...

(Z)-4-Amino-4-oxobut-2-enoic acid Structure

(Z)-4-Amino-4-o...

2-Aminothiophenol Structure

2-Aminothiophenol

~58%

2-(3-oxo-4H-1,4-benzothiazin-2-yl)acetamide Structure

2-(3-oxo-4H-1,4...

2-Butenoic acid,4-[(4-methylphenyl)amino]-4-oxo-, (2Z)- Structure

2-Butenoic acid...

2-Aminothiophenol Structure

2-Aminothiophenol

~81%

2-[4-(4-methylphenyl)-3-oxo-1,4-benzothiazin-2-yl]acetamide Structure

2-[4-(4-methylp...

methyl 4-(4-methylanilino)-4-oxobut-2-enoate Structure

methyl 4-(4-met...

2-Aminothiophenol Structure

2-Aminothiophenol

~83%

2-[4-(4-methylphenyl)-3-oxo-1,4-benzothiazin-2-yl]acetamide Structure

2-[4-(4-methylp...

p Tolylmaleimide Structure

p Tolylmaleimide

2-Aminothiophenol Structure

2-Aminothiophenol

~%

2-[4-(4-methylphenyl)-3-oxo-1,4-benzothiazin-2-yl]acetamide Structure

2-[4-(4-methylp...

2(5H)-Furanone,5-[(4-methylphenyl)imino]- Structure

2(5H)-Furanone,...

2-Aminothiophenol Structure

2-Aminothiophenol

~%

2-[4-(4-methylphenyl)-3-oxo-1,4-benzothiazin-2-yl]acetamide Structure

2-[4-(4-methylp...

(Z)-3-(prop-2-enylcarbamoyl)prop-2-enoic acid Structure

(Z)-3-(prop-2-e...

2-Aminothiophenol Structure

2-Aminothiophenol

~56%

2-(3-oxo-4H-1,4-benzothiazin-2-yl)-N-prop-2-enylacetamide Structure

2-(3-oxo-4H-1,4...

A New Synthesis of Some 2-Substituted-3, 4-dihydro-3-oxo-1, ...

[Kirchner; Alexander Journal of the American Chemical Society, 1959 , vol. 81, p. 1721,1722]

A New Synthesis of Some 2-Substituted-3, 4-dihydro-3-oxo-1, ...

[Kirchner; Alexander Journal of the American Chemical Society, 1959 , vol. 81, p. 1721,1722]