Synthesis of 2-Amino-2′-hydroxy-1,1′-biaryls via Cascade Benzannulation and C-N Bond Cleavage Sequence

Raju Adepu, Jadhav Rahul Dhanaji, Polasani Samatha, Prathama S. Mainkar, Srivari Chandrasekhar

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

A serendipitous synthesis of N-substituted 2-amino-2′-hydroxy-1,1′-biaryls through an aryne annulation with indolyl β-ketonitrile/ester in a cascade manner is demonstrated. The reaction sequence involves benzyne-mediated [2 + 2] Stoltz-type cycloaddition-cleavage and intramolecular Michael addition followed by C-N bond cleavage under transition-metal-free reaction conditions. Interestingly, while [4 + 2] Diels-Alder reaction is a possible pathway, no traces of the regioisomer was isolated.

Original languageEnglish
Pages (from-to)8224-8228
Number of pages5
JournalOrganic Letters
Volume22
Issue number21
DOIs
StatePublished - 6 Nov 2020
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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