AI Article Synopsis
- A new method has been developed to synthesize various functionalized quinazolinones using a series of reactions involving Pd-catalyzed coupling and electrocyclization.
- When a specific type of compound (3-(2-isocyanoethyl)indoles) is used, there’s an interesting competition between two reactions, leading to the formation of different products.
- This process allows for a modular and highly selective synthesis of both quinazolinones and spiroindolenine-3,3'-pyrrolo[2,1-]quinazolinones.
Article Abstract
A general protocol for the synthesis of a variety of functionalized quinazolinones has been developed through a sequential Pd-catalyzed coupling/1,5-alkyloxy/thio/azole shift/6π electrocyclization reaction of isocyanides and 2-carbonylaryl azides. When 3-(2-isocyanoethyl)indoles were utilized, an unusual competitive reaction between [1,5]-shift and indole-spirocyclization was observed, which renders a modular synthesis of quinazolinones and spiroindolenine-3,3'-pyrrolo[2,1-]quinazolinones in a highly chemoselective manner.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.4c04008 | DOI Listing |
Publication Analysis
Top Keywords
[15]-oxy/thio/azole sigmatropic
4
sigmatropic rearrangement
4
rearrangement versus
4
versus indolyl-spirocyclization
4
indolyl-spirocyclization tandem
4
tandem reactions
4
reactions 2-azidobenzoate
4
2-azidobenzoate isocyanides
4
isocyanides accessing
4
accessing quinazolin-43-ones
4
Similar Publications
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!