Fluorescence reagents. I. Derivatization of carboxylic acids,imides and alcohols with 1-chloromethylbenz[c,d]indol-2(1H)-one (CMBI)

The derivatization and fluorodensitometric determination of carboxylic acids (CA), imides and alcohols with 1-chloromethylbenzc,d]indol-2(1H)-one ( 19 , CMBI) have been studied. Out of a series of fluorescent fused lactams 9-11, 13-15 and 17 , benzindolone 17 was selected and transformed via hydroxymethylbenzin-dolone 18 into CMBI 19. CMBI reacts with CA, diCA and alcohols respectively to yield strongly fluorescent benzc,d]indol-1-ylmethyl esters 20, 21 (BIM esters) and BIM ethers 22. Phenobarbital is transformed by action of CMBI into fluorescent 1,3-bisBIM phenobarbital 25. Studies on the applicability of the derivatization reactions to the fluorodensitometric determination of CA, alcohols and imides showed that CA with more than 3 carbon atoms can be determined via BIM esters down to the low picomole range. In the case of alcohols and imides the results were not satisfying. The ir, uv, fluorescence, nmr and mass spectra of the prepared benzindole derivatives are also presented.