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

Bromine oxidation of N-(3 or 4-substituted phenyl)-N'-3-phenylpropenoylthioureas

M Dzurilla, P Kristian, J Imrich…

Index: Dzurilla, Milan; Kristian, Pavol; Imrich, Jan; Stec, Juraj Collection of Czechoslovak Chemical Communications, 1983 , vol. 48, # 11 p. 3134 - 3139

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Citation Number: 6

Abstract

Abstract Bromine oxidation of N-(3 or 4-substituted phenyl)-N'-3-phenylpropenoylthioureas in chloroform afforded either derivatives of benzylidenethiazoline or benzothiazole depending on the structure of the aniline residue. The structure of the title products was proved by elemental analysis, IR, 1 H NMR and 13 C NMR spectral data.

N-[(4-nitrophenyl)carbamothioyl]-3-phenylprop-2-enamide Structure

N-[(4-nitrophen...

~60%

5-benzylidene-2-(4-nitroanilino)-1,3-thiazol-4-one Structure

5-benzylidene-2...

trans-3-Phenylpropenoyl isothiocyanate Structure

trans-3-Phenylp...

~%

5-benzylidene-2-(4-nitroanilino)-1,3-thiazol-4-one Structure

5-benzylidene-2...

4-Nitroaniline Structure

~%

5-benzylidene-2-(4-nitroanilino)-1,3-thiazol-4-one Structure

5-benzylidene-2...

N-(3-Bromophenyl)-N'-3-phenylpropenoylthiourea Structure

N-(3-Bromopheny...

~21%

5-benzylidene-2-(3-bromoanilino)-1,3-thiazol-4-one Structure

5-benzylidene-2...

trans-3-Phenylpropenoyl isothiocyanate Structure

trans-3-Phenylp...

~%

5-benzylidene-2-(3-bromoanilino)-1,3-thiazol-4-one Structure

5-benzylidene-2...

3-Bromoaniline Structure

~%

5-benzylidene-2-(3-bromoanilino)-1,3-thiazol-4-one Structure

5-benzylidene-2...

N-[(3-nitrophenyl)carbamothioyl]-3-phenylprop-2-enamide Structure

N-[(3-nitrophen...

~47%

5-benzylidene-2-(3-nitroanilino)-1,3-thiazol-4-one Structure

5-benzylidene-2...

trans-3-Phenylpropenoyl isothiocyanate Structure

trans-3-Phenylp...

~%

5-benzylidene-2-(3-nitroanilino)-1,3-thiazol-4-one Structure

5-benzylidene-2...

3-Nitroaniline Structure

~%

5-benzylidene-2-(3-nitroanilino)-1,3-thiazol-4-one Structure

5-benzylidene-2...

N-(3-Methoxyphenyl)-N'-3-phenylpropenoylthiourea Structure

N-(3-Methoxyphe...

~65%

N-(5-methoxy-1,3-benzothiazol-2-yl)-3-phenylprop-2-enamide Structure

N-(5-methoxy-1,...

trans-3-Phenylpropenoyl isothiocyanate Structure

trans-3-Phenylp...

~%

N-(5-methoxy-1,3-benzothiazol-2-yl)-3-phenylprop-2-enamide Structure

N-(5-methoxy-1,...

3-anisidine Structure

~%

N-(5-methoxy-1,3-benzothiazol-2-yl)-3-phenylprop-2-enamide Structure

N-(5-methoxy-1,...

N-(3-Hydroxylphenyl)-N'-3-phenylpropenoylthiourea Structure

N-(3-Hydroxylph...

~51%

N-(5-hydroxy-1,3-benzothiazol-2-yl)-3-phenylprop-2-enamide Structure

N-(5-hydroxy-1,...

N-(4-Bromophenyl)-N'-3-phenylpropenoylthiourea Structure

N-(4-Bromopheny...

~40%

5-benzylidene-2-(4-bromoanilino)-1,3-thiazol-4-one Structure

5-benzylidene-2...

trans-3-Phenylpropenoyl isothiocyanate Structure

trans-3-Phenylp...

~%

5-benzylidene-2-(4-bromoanilino)-1,3-thiazol-4-one Structure

5-benzylidene-2...

4-Bromoaniline Structure

~%

5-benzylidene-2-(4-bromoanilino)-1,3-thiazol-4-one Structure

5-benzylidene-2...

trans-3-Phenylpropenoyl isothiocyanate Structure

trans-3-Phenylp...

4-Nitroaniline Structure

~83%

N-[(4-nitrophenyl)carbamothioyl]-3-phenylprop-2-enamide Structure

N-[(4-nitrophen...

trans-3-Phenylpropenoyl isothiocyanate Structure

trans-3-Phenylp...

3-Nitroaniline Structure

~75%

N-[(3-nitrophenyl)carbamothioyl]-3-phenylprop-2-enamide Structure

N-[(3-nitrophen...