Article
2023
·
4 citations
Acetic Acid-Catalyzed 1,6-Addition of Indolizine to <i>para</i>-Quinone Methides
Abstract
This article describes the development of a metal and additive-free protocol that utilizes acetic acid (AcOH) as a catalyst for the C3-alkylation of indolizines using para-Quinone Methides (p-QMs) as an alkylation agent. The metal and additive free method offers an easy route to various substituted indolizine derivatives with good functional group tolerance and delivering acceptable good yields (up to 93%). A gram-scale synthesis and further product derivatization show the synthetic potential of this technique. The significance of these findings for medicinal chemistry makes this easy and green approach relevant to both medicinal and synthetic organic chemists, given the crucial role of indolizine in the pharmaceutical industry.
Keywords
1
6-Nucleophilic addition
Bronsted acid
C3-alkylation
Indolizine
para-Quinone Methides
1,6-CONJUGATE ADDITION
C3 FUNCTIONALIZATION
BIOLOGICAL-ACTIVITY
CONJUGATE ADDITION
DERIVATIVES
ANNULATION
ARYLATION
INDOLES
ACCESS
WoS Categories
Chemistry, Organic
Sustainable Development Goals
Citation
- Journal
- ASIAN JOURNAL OF ORGANIC CHEMISTRY
- Year
- 2023
- Volume
- 12
- Issue
- 7
- ISSN
- 2193-5807
- eISSN
- 2193-5815
- DOI
- 10.1002/ajoc.202300202
- WoS UID
- WOS:001004525100001