Synthesis Of Chiral Fluorescent Reagents

In this paper, we described the synthesis of chiral fluorescent analytical reagent according to the basic theory of organic chemistry. We selected the anthracene and acridine as the basic molecule of fluorescence, and designed two types of chiral fluorescent analytical reagents suit for detecting amino acids and amines, meanwhile, we investigated the synthesis of analytical detecting reagent. The main work as following:1. The synthesis of (R)-(+)-N-(9-Anthracenyl)Proline Acetyl Chloride, (R)-(+)-N-(9-acridinyl) Acetyl Chloride and (R)-(+)-N-(9- anthracenyl) -3 -isothiocyanatopyrrolidine.2. In the course of the synthesis of (R)-(+)-N-(9-anthracenyl) -Proline Acetyl Chloride, the yield of 10-nitro-9-fluoroanthracene is very low. The reactions of 10-nitro-9-fluoroanthracene and Proline are sensitive to temperature and pH value, and the product is very inconstancy. In the course of separation, the product decomposed and returned to the starting material of the reaction. Although many methods have been attampted, the result is still unsatisfactory;In the course of the synthesis of (R)-(+)- N-(9- acridinyl) Proline Acetyl Chloride, It is likely 9-chloro acridine cann't react with Proline easily because of the space hindrance and unhomogeneoussystem, the ultimately product is 9-hydroxyacridine; In the course of the synthesis of (R)-(+)- N-(9-anthracenyl) -3-isothiocyanatopyrrolidine, we synthesized nine compounds, three compounds amount of them are not reported in previously literatures. And the quantum of catalyzer used in the reduction of amino-protection was also studied.3. In the course of the reduction of (R)-(+)-N-(9-anthracenyl)--3-amino-2,5-pyrrolidinedione, perhaps the C-N bond of anthracene and substituent is sensitive to heat or strong acidity and alkalinity, the ultimately main production we seperated is Anthracene. Then we tried to modify the amino group to form (R)-(+)-N-(9-anthracenyl) -3-isothiocyanatopyrrolidinedione, but this compound is still very inconstancy, and difficultly to purificate due to the existance of two carbonyl groups.