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Simultaneous reduction of the nitro group and the azide group in o-nitrophenylazide induced by the TiCl4/Sm system: a novel synthesis of 2,3-dihydro-1H-1,5-benzodiazepines

✍ Scribed by Weihui Zhong; Yongmin Zhang; Xiaoyuan Chen

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 76 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)01888-8

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✦ Synopsis

o-Nitrophenylazide was treated with the low-valent titanium reagent derived from the TiCl 4 /Sm system to produce the intermediate 2 in situ, which was a 'living' double-anion and reacted readily with ketones containing active methyl or methylene groups to afford 2,3-dihydro-1H-1,5-benzodiazepines in moderate to high yields under mild and neutral conditions.

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