Synthesis and NMR study of 9′‐substituted spiroindolinonaphthoxazine derivatives

Abstract

Abstract A photochromic spiroindolinonaphthoxazine derivative, 1,3,3‐trimethyl‐9′‐hydroxy‐spiro[indoline‐2,3′(3 H )‐ naphtho[2,1‐ b ][1,4]oxazine] 3 was synthesized by condensation of 1,2,3,3‐tetramethylindolenium iodide 1 and l‐nitroso‐2,7‐dihydroxynaphthalene 2 . Further, two new derivatives, 5 and 7 , were prepared in good yields by the reactions of 3 with the hexafluoropropene trimer 4 and 4‐[perfluoro(2‐isopropyl‐1,3‐dimethyl‐1‐butenyl)‐oxybenzoyl chloride 6 , respectively. Their unique structural features and property are discussed based on 1 H‐, 13 C‐ and 19 F nmr spectral data.