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

Tetrahedron

Heterocyclic syntheses via carbanionically induced rearrangement reactions

D Hellwinkel, R Lenz, F Lämmerzahl

Index: Hellwinkel, Dieter; Lenz, Ruediger; Lammerzahl, Frank Tetrahedron, 1983 , vol. 39, # 12 p. 2073 - 2084

Full Text: HTML

Citation Number: 11

Abstract

The easily occurring [1.3]-migrations of sulfonyl and carbonyl functions to neighboring phenyl anions can be utilized for ring expansions by one benzo unit when suitably tailored precursor heterocycles are used. Thus, the 1, 2-benzisothiazol dioxide systems 8 and 17 can be transformed into di-benzo [b, f][1, 4] thiazepin dioxides 12 and 21, respectively, whereas the dibenzo [c, e][1, 2]-and 1, 2, 4-benzothiazin dioxide models 35 and 46 give ...

N-(2-bromo-4-methylphenyl)-2-[[2-[(2-bromo-4-methylphenyl)carbamoyl]phenyl]disulfanyl]benzamide Structure

N-(2-bromo-4-me...

~75%

2-(2-bromo-4-methylphenyl)-1,2-benzothiazol-3-one Structure

2-(2-bromo-4-me...

N-(2-Bromo-4-methylphenyl)benzamide Structure

N-(2-Bromo-4-me...

~%

1,3-bis(2-bromo-4-methylphenyl)urea Structure

1,3-bis(2-bromo...

2-Bromo-p-toluidine Structure

2-Bromo-p-toluidine

Ethyl chloroformate Structure

Ethyl chloroformate

~%

1,3-bis(2-bromo-4-methylphenyl)urea Structure

1,3-bis(2-bromo...

N-benzoyl-N-(2-bromo-4-methylphenyl)benzamide Structure

N-benzoyl-N-(2-...

~%

1,3-bis(2-bromo-4-methylphenyl)urea Structure

1,3-bis(2-bromo...

N-(2-(1-hydroxy-2,2-dimethyl-1-phenylpropyl)-4-methylphenyl)benzamide Structure

N-(2-(1-hydroxy...

N-(4-methyl-2-(6-methyl-2,4-diphenyl-4H-benzo[d][1,3]oxazin-4-yl)phenyl)benzamide Structure

N-(4-methyl-2-(...

2-(2-bromo-4-methylphenyl)-1,2-benzothiazol-3-one Structure

2-(2-bromo-4-me...

~52%

2-(2-bromo-4-methylphenyl)-1-oxo-1,2-benzothiazol-3-one Structure

2-(2-bromo-4-me...

N-(2-bromo-4-methylphenyl)-2-[[2-[(2-bromo-4-methylphenyl)carbamoyl]phenyl]disulfanyl]benzamide Structure

N-(2-bromo-4-me...

~%

2-(2-bromo-4-methylphenyl)-1-oxo-1,2-benzothiazol-3-one Structure

2-(2-bromo-4-me...

2-(2-bromo-4-methylphenyl)-1-oxo-1,2-benzothiazol-3-one Structure

2-(2-bromo-4-me...

~%

N-(2-bromo-4-methylphenyl)-2-[[2-[(2-bromo-4-methylphenyl)carbamoyl]phenyl]disulfanyl]benzamide Structure

N-(2-bromo-4-me...

2-(2-iodophenyl)aniline Structure

2-(2-iodophenyl...

~%

5-methyl-6-(4-methylphenyl)phenanthridin-5-ium,chloride Structure

5-methyl-6-(4-m...

p-toluoyl chloride Structure

p-toluoyl chloride

~%

5-methyl-6-(4-methylphenyl)phenanthridin-5-ium,chloride Structure

5-methyl-6-(4-m...

5-methyl-6-p-tolyl-phenanthridinium, methyl sulfate Structure

5-methyl-6-p-to...

~%

5-methyl-6-(4-methylphenyl)phenanthridin-5-ium,chloride Structure

5-methyl-6-(4-m...

N-(2'-iodo-2-biphenylyl)-N,4-dimethylbenzamide Structure

N-(2'-iodo-2-bi...

~%

5-methyl-6-(4-methylphenyl)phenanthridin-5-ium,chloride Structure

5-methyl-6-(4-m...

N-(2'-iodo-2-biphenylyl)-4-methylbenzamide Structure

N-(2'-iodo-2-bi...

~%

5-methyl-6-(4-methylphenyl)phenanthridin-5-ium,chloride Structure

5-methyl-6-(4-m...

N-(2-bromo-4-methylphenyl)-2-[[2-[(2-bromo-4-methylphenyl)carbamoyl]phenyl]disulfanyl]benzamide Structure

N-(2-bromo-4-me...

~%

N-(2-bromo-4-methylphenyl)-2-butylsulfanylbenzamide Structure

N-(2-bromo-4-me...

n-Butyllithium Structure

2-(2-bromo-4-methylphenyl)-1,2-benzothiazol-3-one Structure

2-(2-bromo-4-me...

~%

N-(2-bromo-4-methylphenyl)-2-butylsulfanylbenzamide Structure

N-(2-bromo-4-me...

N-(2-bromo-4-methylphenyl)-2-[[2-[(2-bromo-4-methylphenyl)carbamoyl]phenyl]disulfanyl]benzamide Structure

N-(2-bromo-4-me...

~%

N-(2-bromo-4-methylphenyl)-2-tert-butylsulfanylbenzamide Structure

N-(2-bromo-4-me...

Tert-Butyllithium Structure

Tert-Butyllithium

2-(2-bromo-4-methylphenyl)-1,2-benzothiazol-3-one Structure

2-(2-bromo-4-me...

~%

N-(2-bromo-4-methylphenyl)-2-tert-butylsulfanylbenzamide Structure

N-(2-bromo-4-me...

N-(2-bromo-4-methylphenyl)-2-phenylbenzamide Structure

N-(2-bromo-4-me...

~23%

5-(2-bromo-4-methylphenyl)phenanthridin-6-one Structure

5-(2-bromo-4-me...

2-Bromo-p-toluidine Structure

2-Bromo-p-toluidine

~%

5-(2-bromo-4-methylphenyl)phenanthridin-6-one Structure

5-(2-bromo-4-me...

2-phenylbenzoyl chloride Structure

2-phenylbenzoyl...

~%

5-(2-bromo-4-methylphenyl)phenanthridin-6-one Structure

5-(2-bromo-4-me...

2-Bromo-p-toluidine Structure

2-Bromo-p-toluidine

2-phenylbenzoyl chloride Structure

2-phenylbenzoyl...

~82%

N-(2-bromo-4-methylphenyl)-2-phenylbenzamide Structure

N-(2-bromo-4-me...

2-Bromo-p-toluidine Structure

2-Bromo-p-toluidine

o-Nitrophenylsulfonyl chloride Structure

o-Nitrophenylsu...

~90%

N-(2-bromo-4-methylphenyl)-2-nitrobenzenesulfonamide Structure

N-(2-bromo-4-me...

N-(2-bromo-4-methylphenyl)-2-nitrobenzenesulfonamide Structure

N-(2-bromo-4-me...

~87%

2-amino-N-(2-bromo-4-methylphenyl)benzenesulfonamide Structure

2-amino-N-(2-br...

2-Bromo-p-toluidine Structure

2-Bromo-p-toluidine

~%

2-amino-N-(2-bromo-4-methylphenyl)benzenesulfonamide Structure

2-amino-N-(2-br...

o-Nitrophenylsulfonyl chloride Structure

o-Nitrophenylsu...

~%

2-amino-N-(2-bromo-4-methylphenyl)benzenesulfonamide Structure

2-amino-N-(2-br...

2-methyl-12-phenyl-5H-dibenzo[c,g][1,2,6]thiadiazocin 6,6-dioxide Structure

2-methyl-12-phe...

~82%

2-amino-N-(2-benzoyl-4-methylphenyl)benzenesulfonamide Structure

2-amino-N-(2-be...

N-(2-benzoyl-4-methylphenyl)-2-nitrobenzenesulfonamide Structure

N-(2-benzoyl-4-...

~83%

2-amino-N-(2-benzoyl-4-methylphenyl)benzenesulfonamide Structure

2-amino-N-(2-be...

2-Bromo-p-toluidine Structure

2-Bromo-p-toluidine

~%

2-amino-N-(2-benzoyl-4-methylphenyl)benzenesulfonamide Structure

2-amino-N-(2-be...

2-amino-N-(2-bromo-4-methylphenyl)benzenesulfonamide Structure

2-amino-N-(2-br...

~%

2-amino-N-(2-benzoyl-4-methylphenyl)benzenesulfonamide Structure

2-amino-N-(2-be...

N-(2-bromo-4-methylphenyl)-2-nitrobenzenesulfonamide Structure

N-(2-bromo-4-me...

~%

2-amino-N-(2-benzoyl-4-methylphenyl)benzenesulfonamide Structure

2-amino-N-(2-be...

p-Toluidine Structure

~%

2-amino-N-(2-benzoyl-4-methylphenyl)benzenesulfonamide Structure

2-amino-N-(2-be...

Benzoyl chloride Structure

Benzoyl chloride

~%

2-amino-N-(2-benzoyl-4-methylphenyl)benzenesulfonamide Structure

2-amino-N-(2-be...

(2-AMINO-5-METHYLPHENYL)(PHENYL)METHANONE Structure

(2-AMINO-5-METH...

~%

2-amino-N-(2-benzoyl-4-methylphenyl)benzenesulfonamide Structure

2-amino-N-(2-be...

2-(2-bromo-4-methylphenyl)-3-phenyl-2H-1,2,4-benzothiadiazin 1,1-dioxide Structure

2-(2-bromo-4-me...

~%

2-amino-N-(2-benzoyl-4-methylphenyl)benzenesulfonamide Structure

2-amino-N-(2-be...

o-Nitrophenylsulfonyl chloride Structure

o-Nitrophenylsu...

~%

2-amino-N-(2-benzoyl-4-methylphenyl)benzenesulfonamide Structure

2-amino-N-(2-be...

p-Toluidine Structure

~%

N-(4-methylphenyl)-2-pentanoylbenzenesulfonamide Structure

N-(4-methylphen...

methyl 2-chlorosulfonylbenzoate Structure

methyl 2-chloro...

~%

N-(4-methylphenyl)-2-pentanoylbenzenesulfonamide Structure

N-(4-methylphen...

Carbon dioxide Structure

N-methyl-N-(4-methylphenyl)benzenesulfonamide Structure

N-methyl-N-(4-m...

~%

2-[5-methyl-2-(methylamino)phenyl]sulfonylbenzoic acid Structure

2-[5-methyl-2-(...

Phthalic anhydride Structure

Phthalic anhydride

2-Bromo-p-toluidine Structure

2-Bromo-p-toluidine

~90%

2-(2-bromo-4-methylphenyl)isoindole-1,3-dione Structure

2-(2-bromo-4-me...

N-(2-Bromo-4-methylphenyl)benzamide Structure

N-(2-Bromo-4-me...

Benzoyl chloride Structure

Benzoyl chloride

~80%

N-benzoyl-N-(2-bromo-4-methylphenyl)benzamide Structure

N-benzoyl-N-(2-...

Novel Alternative for the NS Bond Formation and Its Applicat...

[Correa, Arkaitz; Tellitu, Imanol; Dominguez, Esther; SanMartin, Raul Organic Letters, 2006 , vol. 8, # 21 p. 4811 - 4813]

Novel Alternative for the NS Bond Formation and Its Applicat...

[Correa, Arkaitz; Tellitu, Imanol; Dominguez, Esther; SanMartin, Raul Organic Letters, 2006 , vol. 8, # 21 p. 4811 - 4813]