One-Pot Synthesis of 6′-Amino-Substituted Spirooxazines
作者:O. A. Fedorova、A. V. Koshkin、V. Lokshin、A. Samat、S. P. Gromov
DOI:10.1055/s-2005-870006
日期:——
A one-pot synthesis of 6'-amino-substituted spiroindolinonaphth[2,1-b][1,4]oxazines is developed through the condensation of 2-methylene-1,3,3-trimethylindoline derivatives and 1-amino-2-naphthol in the presence of different secondary amines and oxidizing agents using methanol or toluene as the solvent. The main advantage of the method is its simplicity, and starting from readily accessible reagents
One-Pot Synthesis of Photochromic 6′-Amino-Substituted Spirooxazines from 1-Nitroso-2-naphthol Zinc Chelate and Indoline Base
作者:Mei-Li Pang、Ji-Ben Meng、Hui-Juan Zhang、Pei-Pei Liu、Zhi-Hong Zou、Jie Han
DOI:10.1055/s-0030-1258197
日期:2010.10
A series of spirooxazine derivatives containing nitrogen heterocycles were synthesized through the condensation of 2-methylene-1,3,3-trimethylindoline derivatives with the zinc salt of 1-nitroso-2-naphthol using ethanol as solvent. The method is simple, starts from readily accessible and inexpensive reagents, and leads to the synthesis of 6′-substituted spirooxazines in moderate to good yields. We simplified the workup and found that, for some target compounds, recrystallization can effectively improve efficiency of the separation and purification.
A plastic organic photochromic article, typically a lens such as an ophthalmic lens or a window such as a vehicle roof light, comprising a plastics host material having a photochromic compound incorporated therein or applied thereto, the article being characterised in that it exhibits the following properties, measured at Air Mass 2 at 25 °C:
(a) an integrated visible transmission in the faded state (B.IVT) ranging from 90 to 25 %,
(b) an integrated visible transmission in the darkened state (D.IVT) ranging from 1 to 50 %, preferably 4 to 30 %,
(c) the rate of darkening of the article when it is exposed to actinic radiation is such that 88% of the darkening range is achieved in 30 seconds or less, i.e.TB8 30 secs,
(d) the rate of fading of the article from its fully darkened condition is such that more than 60 % of the optical density range is recovered in 60 seconds, i.e. % ODG-1 60%, and
(e) the induced optical density of the article, i.e. the change in the optical density of the article, in moving from the faded state (B.IVT) to the darkened state (D.IVT), is greater than 0.45.
Typically, the photochromic compound is a spiro-oxazine compound of general formula (II),