title: Oxidative difunctionalization of 2-amino-4H-pyrans in iodobenzene diacetate and N-chlorosuccinimide: reactivity, mechanistic insights, and DFT calculations.
abstract: Oxidative difunctionalization of 2-amino-4H-pyrans was accomplished with iodobenzene diacetate (IBD) and N-chlorosuccinimide (NCS) reagents in alcoholic medium. 2-Amino-4H-pyrans undergo geminal dialkoxylation with the migration of an amino group (1a,b, 2a-i, 3a,b, and 4) in IBD, whereas with NCS addition of both chlorine and alkoxy groups takes place across the chromene double bond (6a-i).
authors.affiliation: Crop Protection Chemicals, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500607, India.
authors.forename: Santhosh Reddy
authors.initials: SR
authors.lastname: Mandha
authors.forename: Manjula
authors.initials: M
authors.lastname: Alla
authors.forename: Vittal Rao
authors.initials: VR
authors.lastname: Bommena
authors.forename: Jagadeesh Babu
authors.initials: JB
authors.lastname: Nanubolu
authors.forename: Santosh Kumar
authors.initials: SK
authors.lastname: Lingala
authors.forename: Soujanya
authors.initials: S
authors.lastname: Yarasi
mesh_terms: D007462:Iodobenzenes / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011714:Pyrans / Q000737:chemistry*; D011789:Quantum Theory; D013388:Succinimides / Q000737:chemistry*
chemical_list: D007462:Iodobenzenes; D011714:Pyrans; D013388:Succinimides; C015752:N-chlorosuccinimide; C031905:iodobenzene