Synthesis and NMR study of 9′‐substituted spiroindolinonaphthoxazine derivatives | Zendy

Kakishita Tomonari | Zendy; Matsumoto Kiyoichi | Zendy; Kiyotsukuri Tsuyoshi | Zendy; Matsumura Kenji | Zendy; Hosoda Masahiro | Zendy

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Synthesis and NMR study of 9′‐substituted spiroindolinonaphthoxazine derivatives

Author(s) -

Kakishita Tomonari,

Matsumoto Kiyoichi,

Kiyotsukuri Tsuyoshi,

Matsumura Kenji,

Hosoda Masahiro

Publication year - 1992

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570290706

Subject(s) - chemistry , trimer , indoline , iodide , photochromism , derivative (finance) , condensation , chloride , morpholine , isopropyl , medicinal chemistry , carbon 13 nmr , proton nmr , organic chemistry , dimer , physics , financial economics , economics , thermodynamics

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.

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