Mild, Metal-Free Oxidative Ring-Expansion Approach for the Synthesis of Benzo[b]azepines

S Stockerl, T Danelzik, DG Piekarski… - Organic …, 2019 - ACS Publications
S Stockerl, T Danelzik, DG Piekarski, O García Mancheño
Organic letters, 2019ACS Publications
Benzo [b] azepines are important structural motifs for the pharmaceutical industry. However,
their syntheses are usually lengthy, involving several steps, transition-metal catalysts, and/or
harsh conditions. A novel, general, mild, and metal-free oxidative ring expansion tandem
reaction of hydroquinolines with TMSCHN2 as a versatile soft nucleophile to gain access to
these valuable compounds in a simple and straightforward manner is presented.
Benzo[b]azepines are important structural motifs for the pharmaceutical industry. However, their syntheses are usually lengthy, involving several steps, transition-metal catalysts, and/or harsh conditions. A novel, general, mild, and metal-free oxidative ring expansion tandem reaction of hydroquinolines with TMSCHN2 as a versatile soft nucleophile to gain access to these valuable compounds in a simple and straightforward manner is presented.
ACS Publications
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