Organocatalytic Diastereoselective Synthesis of Diazoaryl-benzo[b]azepine Derivatives

Koppanathi Nagaraju, Ramani Gurubrahamam, Ramani Gurubrahamam, Kwunmin Chen*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

To construct multisubstituted seven-membered nitrogenous heterocyclic scaffolds, an efficient method, employing 2-aminoaryl N-monosubstituted hydrazones and 2-oxo-3-butenoates under Brønsted acid catalysis, has been developed. This strategy highlights the umpolung reactivity of 2-aminobenzaldehyde arylhydrazones toward 2-oxo-3-butenoates to afford (E)-diazoaryl-benzo[b]azepine derivatives in excellent yields (89-99%) and with high diastereoselectivities (>19:1 dr).

Original languageEnglish
Pages (from-to)7060-7067
Number of pages8
JournalJournal of Organic Chemistry
Volume85
Issue number11
DOIs
Publication statusPublished - 2020 Jun 5

ASJC Scopus subject areas

  • Organic Chemistry

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