1999
DOI: 10.1016/s1381-5148(97)00180-6
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Synthesis, characterization and controlled release behaviour of adducts from chloroacetylated cellulose and α-naphthylacetic acid

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Cited by 38 publications
(21 citation statements)
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“…The third stepwas achieved bythe synthesisof7(Chloro-acetic acid 3-((3-chloro-2-oxocyclobutyl)-{2-[(3-chloro-2-oxo-cyclobutyl)- [1,10] phenanthrolin-5-ylmethyl-amino]ethyl}-amino)-10,13-dimethyl-2, 3,6,7,8,9,10,11,12, 13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester)byreactionof 5with chloroacetylchloride in the presenceoftriet-hylamine.This method has been previously reported for other type of compound withbothaminoand iminogroupsinvolved in its structure chemical, which react with chloroacetylchloride to form cyclobutanone groups 16 .However, it isnoteworthy that hydroxylgroupof compound 5 was esterified with acetylchloride. This phenomenon is similar to esterification of other type of compounds 17,18 . ppm for cyclobutanone groups; at 40.80 ppm for methylene group bound to both ester and chloride groups; at 50.02 and 53.07 ppm for methylene groups bound to both amino groups; at 57.28 ppm for methylene group bound to both amino and phenyl groups; at 120.38, 124.45-145.02 and 148.12-155.33 ppm for phenanthroline group; at 168.14 ppm for ester group; at 201.34 and 202.22 ppm for ketone groups.…”
Section: Resultssupporting
confidence: 77%
“…The third stepwas achieved bythe synthesisof7(Chloro-acetic acid 3-((3-chloro-2-oxocyclobutyl)-{2-[(3-chloro-2-oxo-cyclobutyl)- [1,10] phenanthrolin-5-ylmethyl-amino]ethyl}-amino)-10,13-dimethyl-2, 3,6,7,8,9,10,11,12, 13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester)byreactionof 5with chloroacetylchloride in the presenceoftriet-hylamine.This method has been previously reported for other type of compound withbothaminoand iminogroupsinvolved in its structure chemical, which react with chloroacetylchloride to form cyclobutanone groups 16 .However, it isnoteworthy that hydroxylgroupof compound 5 was esterified with acetylchloride. This phenomenon is similar to esterification of other type of compounds 17,18 . ppm for cyclobutanone groups; at 40.80 ppm for methylene group bound to both ester and chloride groups; at 50.02 and 53.07 ppm for methylene groups bound to both amino groups; at 57.28 ppm for methylene group bound to both amino and phenyl groups; at 120.38, 124.45-145.02 and 148.12-155.33 ppm for phenanthroline group; at 168.14 ppm for ester group; at 201.34 and 202.22 ppm for ketone groups.…”
Section: Resultssupporting
confidence: 77%
“…It is important to mention that this method has been previously reported for other type of compound with animino group involved in its structure chemical, which react with chloroacetyl chloride to form an azetine group in presence of triethylamine 10 . However, it is noteworthy that amino group of compound 3also reacting with chloroacetyl chloride to form a new chloroamide group; this method is different to several previously reported procedures for thechloroamides formation 11,12 .The 1 H NMR spectrum of the 3 shows signals at1.64-1.79, 2.84 and 3.06 ppm for piperidine group; at 1.80-2.48 ppm for methylene groups bound to both piperidine and azetidinegroups; at 2.80, 3.84 for methylene groups bound to both azetidine and amide groups; at 4.10 ppm for methylene group bound to chloroacetamide group; at 4.30 ppm for methylene group bound to ester group; at 5.32 ppm for proton involved in the azetidinering; at 6.60 ppm for amide group; at 7.02-7.30 ppm for phenyl groups.The 13 C NMR spectra displays chemical shifts at23.00, 32.80 and 55.28 ppm for methylene groups bound to piperidine and azetidine groups, at 33.98, 46.90and 79.66 ppm for piperidine group; at 35.30 (4-fluoro-phenyl)-butylideneamino]-ethylimino}-methyl)-13-methyl-7,8,9,11,12,13,14,15,16, 17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol (5). Reactionof1with3,17-Dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-2,4-dicarbaldehyde (4)tosynthesisof5 usingboricacid as catalyst (ii) and 49.30 ppm for methylene bound to both azetidine and amide groups, at 42.00 ppm for methylene group bound to ester group; at 42.40 ppm for methylene group bound to chloroacetamide group; at 70.78 and 74.00 ppm for carbons involved in the azetidine group;at 115.08-161.68 ppm for phenyl groups; at 162.58 ppm for amide group; at 166.30 ppm for ketone group; at 167.28 ppm for ester group.…”
Section: Resultsmentioning
confidence: 81%
“…Although the reactivity of the hydroxyl depends heavily of the reagents and the reaction conditions, the hydroxyl group present at the 3-carbon is even less reactive. Thus, the cellulose hydroxyl groups have the following reactivity order: C6 >> C2 > C3, this order being explained by the influence of the formation of inter-and intramolecular hydrogen bonds, as well as the degree of crystallinity, by favoring the water absorption in amorphous regions in comparison with the crystalline this material [55]. The main changes occurring in cellulose are due to halogenation, oxidation, etherification, and esterification.…”
Section: Modification Of Cellulosementioning
confidence: 99%