Altering the Cyclization Modes: Temperature-Dependent Intramolecular 7-Endo-Dig vs 6-Endo-Dig Electrophilic Ring Closures

Maloy Nayak, Young Kee Kang, Ikyon Kim

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

In an attempt to construct 10-acyl-5H-benzo[e]pyrrolo[1,2-a]azepines via acid-catalyzed intramolecular alkyne carbonyl metathesis, two distinctive modes of cyclization were revealed to depend on the reaction temperatures. 5H-Benzo[e]pyrrolo[1,2-a]azepine-1-carbaldehydes with a substituent at the C11 position were obtained as major products at 90 °C as a result of intramolecular 7-endo-dig cyclization, while 6-endo-dig ring closure by electrophilic addition of nitrogen of the pyrrole to a vinyl cation generated under acidic medium followed by an unprecedented domino rearrangement process was observed at 40 °C in some cases, resulting in 5-aryl-11H-benzo[d]pyrrolo[1,2-a]azepine-1-carbaldehydes along with the former products.

Original languageEnglish
Pages (from-to)1474-1477
Number of pages4
JournalOrganic Letters
Volume19
Issue number6
DOIs
Publication statusPublished - 2017 Mar 17

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIP) (2014R1A2A1A11050491) (to I.K.). We thank Mr. Juwon Kang (Yonsei University) for conducting preliminary experiments of this study.

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Altering the Cyclization Modes: Temperature-Dependent Intramolecular 7-Endo-Dig vs 6-Endo-Dig Electrophilic Ring Closures'. Together they form a unique fingerprint.

Cite this