Ligand-free access to benzisothiazolones and benzisoselenazolones through NiFe2O4 catalyzed concomitant annulation of 2-halobenzanilides with chalcogens and their late-stage transformations
- 4 October 2022
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in New Journal of Chemistry
- Vol. 46 (40), 19501-19513
- https://doi.org/10.1039/d2nj04326b
Abstract
The present work demonstrates an efficient ligand-free synthesis of diverse benzisothiazolones and benzisoselenazolones exploiting a magnetically retrievable nano-nickel ferrite catalyst in X–N (X = S, Se) cross-coupling with concurrent annulation of 2-iodobenzanilides and elemental sulphur or selenium. The protocol features the use of the recyclable nano-nickel ferrite catalyst, substrate diversity, cheap sulphur and selenium powder as chalcogenation agents, comparatively low reaction temperature and useful application of synthesized molecules. The rarely explored chemistry of NiFe2O4 towards the X–N cross-coupling reaction well complements conventional methods for the synthesis of S–N or Se–N heterocycles. Nickel ferrite nanoparticles were prepared by a simple hydrothermal method and characterized by using XRD, SEM, TEM, HRTEM, SAED, energy dispersive X-ray spectroscopy, XPS, ICP-AES and FT-IR analyses. The easy recovery of the catalyst and high product conversion make the protocol practically economic. The oxidation prone sulphur in benzisothiazolones is transformed into a variety of saccharin motifs using TBN and oxygen as the right oxidant combination. In addition, both the S–N and Se–N containing heterocycles are scaled up and further transformed into novel C–H functionalized products and selenol derivatives, respectively.Funding Information
- University Grants Commission
- University of Calcutta (UGC Ref. No. 282/ (SC) (CSIR-UGC NET DEC.2016))
This publication has 68 references indexed in Scilit:
- Palladium-catalyzed C–N and C–O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenolsBeilstein Journal of Organic Chemistry, 2012
- An efficient copper mediated synthetic methodology for benzo[d]isothiazol-3(2H)-ones and related sulfur–nitrogen heterocyclesTetrahedron Letters, 2012
- N-Tosylhydrazones: versatile reagents for metal-catalyzed and metal-free cross-coupling reactionsChemical Society Reviews, 2012
- Potent, Selective, and Orally Available Benzoisothiazolone Phosphomannose Isomerase Inhibitors as Probes for Congenital Disorder of Glycosylation IaJournal of Medicinal Chemistry, 2011
- A Multiligand Based Pd Catalyst for C−N Cross-Coupling ReactionsJournal of the American Chemical Society, 2010
- Copper‐Catalyzed Formation of Sulfur–Nitrogen Bonds by Dehydrocoupling of Thiols with AminesEuropean Journal of Organic Chemistry, 2010
- Synthesis of 7-Azabenzisoselenazol- 3(2H)-ones: A New Group of Selenium Containing AntimicrobialsSynthetic Communications, 2003
- Process Development of 1,2-Benzisothiazolin-3(2H)-one by Replacing of the Toxic MaterialsSynlett, 2003
- Ebselen, a Seleno-Organic Antioxidant, Is Neuroprotective After Embolic Strokes in RabbitsStroke, 2003
- A general access to acylstannanesThe Journal of Organic Chemistry, 1989