- Synthesis of Mutagenic Methyl- and Phenyl-substituted 2-Amino-3H-imidazoquinoxalines via 2,1,3-Benzoselenadiazoles
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2-Amino-3-methyl-3H-imidazoquinoxaline, all its derivatives with 1-4 methyl groups in positions 4, 5, 7 and 8, and 2-amino-3,5-dimethyl-7,8-diphenyl-3H-imidazoquinoxaline have been synthesized from the corresponding 6-methylamino-5-nitroquinoxalines through reduction and cyclization with cyanogen bromide.The quinoxalines were obtained from the appropriate α-dicarbonyl compounds and 4-methylamino-3-nitro-1,2-benzenediamines.The latter were prepared from 4-halo-1,2-benzenediamines via 2,1,3-benzoselenadiazoles.The 7- and 8-phenyl derivatives of 2-amino-3,5-dimethyl-3H-imidazoquinoxaline have been synthesized in a slightly different way.
- Grivas, Spiros,Tian, Wei,Ronne, Erik,Lindstroem, Stefan,Olsson, Kjell
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p. 521 - 528
(2007/10/02)
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- Convenient Synthesis of 4-Methoxy-3-nitro-1,2-benzenediamine and its Conversion into 6-Methoxy-5-nitroquinoxalines
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4-Methoxy-3-nitro-1,2-benzenediamine (6) has been prepared through nitration of 5-methoxy-2,1,3-benzoselenadiazole, followed by reductive removal of the selenium.Cyclocondensation of 6 with α-dicarbonyl compounds afforded the title quinoxalines, some of them novel and not easily obtainable by direct nitration.Methyl- or phenylglyoxal gave mixtures of quinoxalines in proportions strongly influenced by the acidity of the reaction medium.
- Grivas, Spiros,Tian, Wei
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p. 1109 - 1113
(2007/10/02)
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- An improved synthesis of 3,8-dimethyl-3H-imidazo[4,5-f]quinoxalin-2-amine ("MeIQx") and its 2-14C-labelled analogue.
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The highly mutagenic title compound (MeIQx) was prepared in 21% overall yield from 4-fluoro-o-phenylenediamine. The 3,7-dimethyl isomer may be obtained as a minor by-product. The 14C-label was introduced in the last step through cyclization with [14C]cyanogen bromide. An alternative synthesis of MeIQx from p-fluoroaniline avoided the separation of isomers but gave poorer yield.
- Grivas,Olsson
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- SYNTHESIS OF 2-AMINO-3,8-DIMETHYLIMIDAZOQUINOXALINE (Me-IQx), A POTENT MUTAGEN ISOLATED FROM FRIED BEEF
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A potent mutagen, 2-amino-3,8-dimethylimidazoquinoxaline (Me-IQx), isolated from fried beef and its 3,7-dimethyl derivative were synthesized from 6-amino-3-methylquinoxaline and 6-amino-2-methylquinoxaline, respectively.These compounds showed strong mutagenic activity towards Salmonella typhimurium TA98 in the presence of S9 Mix.
- Kasai, Hiroshi,Shiomi, Tomoko,Sugimura, Takashi,Nishimura, Susumi
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p. 675 - 678
(2007/10/02)
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