Antitumor Imidazotetrazines. 35. New Synthetic Routes to the Antitumor Drug Temozolomide.

@article{Wang1997AntitumorI3,
  title={Antitumor Imidazotetrazines. 35. New Synthetic Routes to the Antitumor Drug Temozolomide.},
  author={Yongfeng Wang and Malcolm F. G. Stevens and Tze-ming Chan Tm and Donald DiBenedetto and Zhe-xing Ding Zx and Dinesh Gala and Donald Hou and Max Kugelman and William Leong and Shen-chun Kuo Sc and Janet L. Mas and Doris P. Schumacher and Bruce P. Shutts and Lyman B. Smith and Z. J. Zhan and William T. Thomson},
  journal={The Journal of organic chemistry},
  year={1997},
  volume={62 21},
  pages={7288-7294}
}
Three new pathways to the antitumor drug temozolomide (4) have been explored via intermediates 3, 6, and 7. The key intermediate 5-amino-1-(N-methylcarbamoyl)imidazole-4-carboxamide (6) has been successfully converted to 4 in 45% yield by employing sodium nitrite in aqueous tartaric acid at 0-5 degrees C. Compound 6 is prepared from nitrophenyl carbamate 14a and methylamine or directly from 5-aminoimidazole-4-carboxamide (13) and either methyl isocyanate or N-methylcarbamoyl chloride… CONTINUE READING
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