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Synthesis of 3‐Spiro Cycloalkenes Fused 7‐Aza‐2‐indalones from 3,3′‐di‐ or N,3,3′‐tri‐ allyl/homoallyl/pentenyl 7‐Aza‐2‐indalones via Ring Closing Metathesis using Grubbs‐II Catalyst
- Source :
-
ChemistrySelect . 9/13/2023, Vol. 8 Issue 34, p1-7. 7p. - Publication Year :
- 2023
-
Abstract
- A facile and efficient synthesis of 3‐spiro cycloalkene fused 7‐aza‐2‐indalones from 3,3′‐di‐ or N,3,3′‐tri‐ allyl/homoallyl/pentenyl 7‐aza‐2‐indalones via ring‐closing metathesis (RCM) using Grubbs‐II catalyst has been achieved. The scope of the reaction has been demonstrated by synthesizing spiro products of various ring sizes (n=5, 7, and 18), utilizing 2‐indalone/7‐azaindalone and various alkenylation agents such as allyl/homoallyl/pentenyl bromides as substrates. In addition to usual RCM products, a cross metathesis (CM) product was observed when the substrate was N,3,3′‐triallylated derivative from 2‐indalone. Notably, a macrocyclic, 18‐membered bis‐spirodiene of N‐methyl‐7‐azaindalone was observed by means of intermolecular ring‐closing metathesis (RCM‐RCM). Also, Structures of a few representative spiro‐annulated products were evidenced with single crystal XRD analysis. Furthermore, a plausible mechanism for the products is discussed. [ABSTRACT FROM AUTHOR]
- Subjects :
- *METATHESIS reactions
*CYCLOALKENES
*CATALYSTS
*ALKENYLATION
*X-ray diffraction
Subjects
Details
- Language :
- English
- ISSN :
- 23656549
- Volume :
- 8
- Issue :
- 34
- Database :
- Academic Search Index
- Journal :
- ChemistrySelect
- Publication Type :
- Academic Journal
- Accession number :
- 171960984
- Full Text :
- https://doi.org/10.1002/slct.202302522