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

Regiospecific synthesis of the aminoimidazoquinoxaline (IQx) mutagens from cooked foods

DE Bierer, JF O'Connell, JR Parquette…

Index: Bierer, Donald E.; O'Connell, John F.; Parquette, Jon R.; Thompson, Charles M.; Rapoport, Henry Journal of Organic Chemistry, 1992 , vol. 57, # 5 p. 1390 - 1405

Full Text: HTML

Citation Number: 9

Abstract

A versatile regioepecific synthesis has been developed to prepare the six dimethyl-and trimethyl-substituted 2-aminoimidazoquinoxaline (IQx) regioisomera 35, 36, 37, 38, 39, and 40 for complete and unambiguous characterization. The key reaction step in the synthetic sequence for these angular tricycles is a photodehydrohalogenative cyclization of suitably substituted pyrazinylimidazolylethylene intermediates derived from common pyrazine and ...

methyl 2,5-dibromo-3-methylimidazole-4-carboxylate Structure

methyl 2,5-dibr...

~%

2-[2-(2,5-dibromo-3-methylimidazol-4-yl)prop-2-enyl]-6-methylpyrazine Structure

2-[2-(2,5-dibro...

2,6-Dimethylpyrazine Structure

2,6-Dimethylpyrazine

~%

2-[2-(2,5-dibromo-3-methylimidazol-4-yl)prop-2-enyl]-6-methylpyrazine Structure

2-[2-(2,5-dibro...

1-(2,5-dibromo-3-methylimidazol-4-yl)ethanone Structure

1-(2,5-dibromo-...

~%

2-[2-(2,5-dibromo-3-methylimidazol-4-yl)prop-2-enyl]-6-methylpyrazine Structure

2-[2-(2,5-dibro...

tert-butyl 3-(2,5-dibromo-3-methylimidazol-4-yl)-3-oxopropanoate Structure

tert-butyl 3-(2...

~%

2-[2-(2,5-dibromo-3-methylimidazol-4-yl)prop-2-enyl]-6-methylpyrazine Structure

2-[2-(2,5-dibro...

2-(2,5-dibromo-3-methylimidazol-4-yl)-1-(6-methylpyrazin-2-yl)propan-2-ol Structure

2-(2,5-dibromo-...

~%

2-[2-(2,5-dibromo-3-methylimidazol-4-yl)prop-2-enyl]-6-methylpyrazine Structure

2-[2-(2,5-dibro...

N/A Structure

2-[(E)-2-(2,5-dibromo-3-methylimidazol-4-yl)prop-1-enyl]-6-methylpyrazine Structure

2-[(E)-2-(2,5-d...

1-(5-bromo-3-methyl-2-methylsulfanylimidazol-4-yl)-2-(6-methylpyrazin-2-yl)ethanone Structure

1-(5-bromo-3-me...

~99%

1-(5-bromo-3-methyl-2-methylsulfanylimidazol-4-yl)-2-(6-methylpyrazin-2-yl)ethanol Structure

1-(5-bromo-3-me...

2,6-Dimethylpyrazine Structure

2,6-Dimethylpyrazine

~%

1-(5-bromo-3-methyl-2-methylsulfanylimidazol-4-yl)-2-(6-methylpyrazin-2-yl)ethanol Structure

1-(5-bromo-3-me...

methyl 5-bromo-3-methyl-2-methylsulfanylimidazole-4-carboxylate Structure

methyl 5-bromo-...

~%

1-(5-bromo-3-methyl-2-methylsulfanylimidazol-4-yl)-2-(6-methylpyrazin-2-yl)ethanol Structure

1-(5-bromo-3-me...

1-(5-bromo-3-methyl-2-methylsulfanylimidazol-4-yl)-2-(5-methylpyrazin-2-yl)ethanol Structure

1-(5-bromo-3-me...

~87%

2-[(E)-2-(5-bromo-3-methyl-2-methylsulfanylimidazol-4-yl)ethenyl]-5-methylpyrazine Structure

2-[(E)-2-(5-bro...

2,5-Dimethylpyrazine Structure

2,5-Dimethylpyrazine

~%

2-[(E)-2-(5-bromo-3-methyl-2-methylsulfanylimidazol-4-yl)ethenyl]-5-methylpyrazine Structure

2-[(E)-2-(5-bro...

methyl 5-bromo-3-methyl-2-methylsulfanylimidazole-4-carboxylate Structure

methyl 5-bromo-...

~%

2-[(E)-2-(5-bromo-3-methyl-2-methylsulfanylimidazol-4-yl)ethenyl]-5-methylpyrazine Structure

2-[(E)-2-(5-bro...

2-[(E)-2-(5-bromo-3-methyl-2-methylsulfanylimidazol-4-yl)ethenyl]-5-methylpyrazine Structure

2-[(E)-2-(5-bro...

~70%

3,8-dimethyl-2-methylsulfanylimidazo[4,5-f]quinoxaline Structure

3,8-dimethyl-2-...

N-benzyl-3,7-dimethylimidazo[4,5-f]quinoxalin-2-amine Structure

N-benzyl-3,7-di...

~60%

2-Amino-3,7-dimethylimidazo[4,5-f]quinoxaline Structure

2-Amino-3,7-dim...

N-benzyl-3,5,8-trimethylimidazo[4,5-f]quinoxalin-2-amine Structure

N-benzyl-3,5,8-...

~80%

3,5,8-trimethylimidazo(4,5-f)quinoxalin-2-amine Structure

3,5,8-trimethyl...

2,6-Dimethylpyrazine Structure

2,6-Dimethylpyrazine

methyl 2,5-dibromo-3-methylimidazole-4-carboxylate Structure

methyl 2,5-dibr...

~%

1-(2,5-dibromo-3-methylimidazol-4-yl)-2-(6-methylpyrazin-2-yl)ethanone Structure

1-(2,5-dibromo-...

N-benzyl-3,8-dimethylimidazo[4,5-f]quinoxalin-2-amine Structure

N-benzyl-3,8-di...

~74%

MeIQx Structure

2,5-Dimethylpyrazine Structure

2,5-Dimethylpyrazine

~%

1-(5-bromo-3-methyl-2-methylsulfanylimidazol-4-yl)-2-(5-methylpyrazin-2-yl)ethanol Structure

1-(5-bromo-3-me...

methyl 5-bromo-3-methyl-2-methylsulfanylimidazole-4-carboxylate Structure

methyl 5-bromo-...

~%

1-(5-bromo-3-methyl-2-methylsulfanylimidazol-4-yl)-2-(5-methylpyrazin-2-yl)ethanol Structure

1-(5-bromo-3-me...

N-benzyl-3,4,7-trimethylimidazo[4,5-f]quinoxalin-2-amine Structure

N-benzyl-3,4,7-...

~62%

3,4,7-trimethylimidazo[4,5-f]quinoxalin-2-amine Structure

3,4,7-trimethyl...

3,4,7-trimethyl-2-methylsulfanylimidazo[4,5-f]quinoxaline Structure

3,4,7-trimethyl...

~%

3,4,7-trimethylimidazo[4,5-f]quinoxalin-2-amine Structure

3,4,7-trimethyl...

3,4,7-trimethyl-2-methylsulfonylimidazo[4,5-f]quinoxaline Structure

3,4,7-trimethyl...

~%

3,4,7-trimethylimidazo[4,5-f]quinoxalin-2-amine Structure

3,4,7-trimethyl...

methyl 5-bromo-3-methyl-2-methylsulfanylimidazole-4-carboxylate Structure

methyl 5-bromo-...

~%

2-(5-bromo-3-methyl-2-methylsulfanylimidazol-4-yl)-1-(5-methylpyrazin-2-yl)propan-2-ol Structure

2-(5-bromo-3-me...

tert-butyl 3-(5-bromo-3-methyl-2-methylsulfanylimidazol-4-yl)-3-oxopropanoate Structure

tert-butyl 3-(5...

~%

2-(5-bromo-3-methyl-2-methylsulfanylimidazol-4-yl)-1-(5-methylpyrazin-2-yl)propan-2-ol Structure

2-(5-bromo-3-me...

2,6-Dimethylpyrazine Structure

2,6-Dimethylpyrazine

~%

2-[(E)-1-(2,5-dibromo-3-methylimidazol-4-yl)prop-1-en-2-yl]-6-methylpyrazine Structure

2-[(E)-1-(2,5-d...

methyl 2,5-dibromo-3-methylimidazole-4-carboxylate Structure

methyl 2,5-dibr...

~%

2-[(E)-1-(2,5-dibromo-3-methylimidazol-4-yl)prop-1-en-2-yl]-6-methylpyrazine Structure

2-[(E)-1-(2,5-d...

1-(2,5-dibromo-3-methylimidazol-4-yl)-2-(6-methylpyrazin-2-yl)ethanone Structure

1-(2,5-dibromo-...

~%

2-[(E)-1-(2,5-dibromo-3-methylimidazol-4-yl)prop-1-en-2-yl]-6-methylpyrazine Structure

2-[(E)-1-(2,5-d...

1-(2,5-dibromo-3-methylimidazol-4-yl)-2-(6-methylpyrazin-2-yl)propan-1-one Structure

1-(2,5-dibromo-...

~%

2-[(E)-1-(2,5-dibromo-3-methylimidazol-4-yl)prop-1-en-2-yl]-6-methylpyrazine Structure

2-[(E)-1-(2,5-d...

2-(6-methyl-2-pyrazinyl)-1-(2,4-dibromo-1-methyl-5-imidazolyl)propan-1-ol Structure

2-(6-methyl-2-p...

~%

(Z)-2-(6-methyl-2-pyrazinyl)-1-(2,4-dibromo-1-methyl-5-imidazolyl)prop-1-ene Structure

(Z)-2-(6-methyl...

2-[(E)-1-(2,5-dibromo-3-methylimidazol-4-yl)prop-1-en-2-yl]-6-methylpyrazine Structure

2-[(E)-1-(2,5-d...