Back to Search
Start Over
Base‐Promoted Michael Addition/Smiles Rearrangement/ N‐Arylation Cascade: One‐Step Synthesis of 1,2,3‐Trisubstituted 4‐Quinolones from Ynones and Sulfonamides.
- Source :
- Advanced Synthesis & Catalysis; 1/7/2020, Vol. 362 Issue 1, p213-223, 11p
- Publication Year :
- 2020
-
Abstract
- A general, practical, and environmentally friendly protocol to synthesize 1,2,3‐trisubstituted 4‐quinolones from readily available ynones and sulfonamides was developed. The construction of one C−C bond and two C−N bonds via cleavage of one N−S, one C−S, and one C−X (X=F, Cl, Br, O) bond is achieved under transition‐metal‐free conditions in one step. This transformation generates 1 equiv. of sulfur dioxide and 1 equiv. of hydrogen halide as the byproducts. The broad substrate scope and functional group tolerance are demonstrated by 52 examples of 1,2,3‐trisubstituted 4‐quinolones. A preliminary mechanistic study supports a sequential Michael addition/Smiles rearrangement/N‐arylation reaction pathway. [ABSTRACT FROM AUTHOR]
- Subjects :
- SCISSION (Chemistry)
SULFUR dioxide
FUNCTIONAL groups
SULFONAMIDES
Subjects
Details
- Language :
- English
- ISSN :
- 16154150
- Volume :
- 362
- Issue :
- 1
- Database :
- Complementary Index
- Journal :
- Advanced Synthesis & Catalysis
- Publication Type :
- Academic Journal
- Accession number :
- 141131854
- Full Text :
- https://doi.org/10.1002/adsc.201900960