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Selectfluor‐Mediated Synthesis of Fluoro Spiro 3(2 H )‐Furanone Derivatives via Domino Fluorination–Defluorination
Author(s) -
Krishna Swaroop Desireddy,
Ravi Kumar Nagiri,
Nagender Punna,
Jitender Dev Gaddameedi,
Jagadeesh Babu Nanubolu,
Narsaiah Banda
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701668
Subject(s) - selectfluor , chemistry , domino , fluorine , intramolecular force , electrophilic fluorination , transformation (genetics) , medicinal chemistry , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , electrophile , biochemistry , gene
An unprecedented Domino transformation towards diverse fluorinated spiro benzothiazinyl furanone scaffolds has been developed from 1,3‐diketone embedded benzothiazines and Selectfluor through fluorinative intramolecular cyclization. The transformation is triggered by fluorine insertion to form a difluoro intermediate, which is responsible for the formation of fluorinated spiro 3(2 H )‐furanone derivatives. We have also succeeded to synthesize non‐fluorinated spiro 3(2 H )‐furanone derivatives by oxidative cyclization using AgF.