The reaction of leucoquinizarins with alkylenediamines

Abstract

The reaction of leucoquinizarin with ethylenediamine and N-al kylethylenediamines gives two series of products, 1 ,4bisa I ky I a m i n oa n t h ra q u i n o n es and 6 -a I ky lam i n o -1 ,2,3,4 -tetra h y dron a p h t h o [ 2,3f] q u i n oxa I i n e -7,12d i o n es.Higher alkylenediamines give only the 1.4-bisalkylaminoanthraquinones. Analogous reactions with 5,8-dihydrleucoquinizarin are also described. LEUCOQUINIZARIN (I) reacts with alkylamines to give characteristics in that the absorptions are shifted to 1,4-bisalkylaminoanthraquinones (11) which have shorter wavelengths, i.e., 567 and 608 mp with an inflecvisible absorption spectra in 2-methoxyethanol with tion at 530 mp and an additional peak at 435 mp (type peaks at 642 and 594 mv and an inflection at 553-556 I1 spectrum, see Figure 1 in ref. 2). In explanation rnp (type I spectrum, see Figure 1 in ref. 2). Simon re-Simon suggested that in the compounds (IIa) and (IIb) ported the preparation of two compounds of this class &signed thestructures 1,4-di-(2-aminoethylaminoanthra-F. B. Stilmar and M. A. Perkins, ' The Chemistry of Synthetic quinone (1-1~) and 1,4-di-(2-ethylaminoethylamino)-Dyes and Pigments,' ed. H.

Synthesis of colorimetric sensors for isomeric dicarboxylate anions: selective discrimination between maleate and fumarate

“…A synthetic intermediate, 1,4-di-(2-aminoethylamino)anthraquinone (5) was prepared from 2,3-dihydro-9,10-dihydroxy-1,4-anthracenedione. 10 Reaction of 5 with 0.7 equivalents of 4-nitronaphthylisothiocyanate in THF gave 6 in 42% yield. Subsequently, reaction of 6 with the corresponding isothiocyanates in THF afforded the bisthiourea derivatives 1-4 in moderate yields.…”

Solid phase synthesis of anthraquinone peptides and their evaluation as topoisomerase I inhibitors

“…The resin was washed with DMF (3 × 10 ml), DCM (3 × 10 ml), diethyl ether (3 × 10 ml) and dried under reduced pressure. Leuco-quinizarin ( Figure 3b) was prepared from quinizarin ( Figure 3a) by the procedure of Greenhalgh and Hughes [14] and purified by column chromatography before each condensation reaction. Leuco-quinizarin (180 mg, 0.75 mmol, 3 eq.)…”

Hair Dyes

“…158 The patent dealing with quaternary ammonium derivatives of nitro and anthraquinone dyes for hair also included a number of quaternized azo dyes. 5,8-Dihydroxyleucoquinizarin gives the analogous quinoxaline derivative.…”

“…The CH 2 NH 2 (R = H, Me, or Et) under N 2 ; 6, air bubbled in reaction of leucoquinizarin with 2-dialkylaminoethylamines and with 1,3-and 1,4-diaminoalkanes gives the normal 1,4-disubstituted anthraquinones 158. Similar quinoxaline derivatives are obtained when 1-chloroanthraquinone is reacted with ethylenediamine, A 7 -methyl ethylenediamine, and o-phenylenediamine.l59 These results indicate that care should be taken in assigning structures to the reaction products of reactive anthraquinones with 1,2-diamines.intermediate (LXX) is obtained by the reaction of 1,5-dinitronaphthalene (LXIX) with sulfur in oleum at 95°.…”