Catalyst- and Additive-Free Approach to Constructing Benzo-oxazine, Benzo-oxazepine, and Benzo-oxazocine: O Atom Transfer and C═O, C–N, and C–O Bond Formation at Room Temperature

Arnab Ghosh, Rajeev V. Hegde, Haridas B. Rode, Ram Ambre, Manoj Vasisht Mane, Siddappa A. Patil, Balasubramanian Sridhar, Ramesh B. Dateer

Research output: Contribution to journalArticlepeer-review

Abstract

An exclusive synthesis of benzo-oxazine, benzo-oxazepine, and benzo-oxazocine from aryl propanal and 2-(hydroxyamino)phenyl alcohol under metal-free conditions is described. O atom transfer and formation of new C═O, C-N, and C-O bonds occur at room temperature to form six-, seven-, and eight-membered heterocycles under one-pot reaction conditions without using an external oxidant and base. The photophysical properties are studied using ultraviolet-visible absorption and photoluminescence. The mechanistic elucidation is well supported by control experiment and literature precedents.
Original languageEnglish (US)
JournalOrganic Letters
DOIs
StatePublished - Oct 13 2021

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry

Fingerprint

Dive into the research topics of 'Catalyst- and Additive-Free Approach to Constructing Benzo-oxazine, Benzo-oxazepine, and Benzo-oxazocine: O Atom Transfer and C═O, C–N, and C–O Bond Formation at Room Temperature'. Together they form a unique fingerprint.

Cite this