Synthesis and photophysical properties of 1, 4-disubstituted naphthyloxymethyl-N-alkyl naphthimido-1,2,3-triazole

Abstract

Regioselective synthesis of a series of 1,4-disubstituted of naphthoxymethyl-N-alkyl naphthalimide-1,2,3-triazoles employing click reaction is presented. Highly selective and efficient copper(I)-catalysed 1,3-dipolar cyclo addition between 1-naphthylpropargylic ether and azido alkyl naphthalimides yielded the title compounds in 74% to 94%. The structure of all the new 1,2,3-triazoles was characterized by 1 HNMR, 13 C NMR, IR and Mass. The electronic absorption and emission studies revealed that the light absorbing and emitting chromophore is the naphthoxy moiety. There is no extensive delocalization of aromatic π-electrons in the active chromophore which exhibited lower quantum yields and lower Stokes shifts.

Highly selective Cu2+ detection with a naphthalimide-functionalised pillar[5]arene fluorescent chemosensor

“…Commercially available chemical reagents were used as received unless otherwise noted. Compounds 3 , 66 4 49 and 5 67 were synthesised following literature procedures. All reported yields represent isolated yields.…”

Photochemical Reactivity of Naphthol-Naphthalimide Conjugates and Their Biological Activity

“…The key intermediates, 1,8naphthalimide derivatives 4, for the coupling, were prepared in three steps (Scheme 2) in good to excellent yields. These steps involved the alkylation of the imide by dibromides to afford 2 [64], followed by hydrolysis by HMPA and H 2 O to alcohols 3 [65], and oxidation to furnish 4. We tried two oxidation protocols, those of Swern [66] and Dess-Martin [67], both of which produced 4 in good yields.…”

Synthesis and Antimicrobial Activity of 2‐(4‐(Hydroxyalkyl)‐1H‐1,2,3‐triazol‐1‐yl)‐N‐substituted propanamides

“…Triazoles have been reported to exhibit broad biological spectrum as anticancer , anti‐HIV , antitubercular , antioxidant , antitrypanosomal , antimicrobial , anticonvulsant , antimalarial , antihistamines , antitumor , immune potentiators , antiviral , anti‐inflammatory and , agents. In addition to aforementioned medicinal value, several members of the 1,2,3‐triazoles family also show interesting industrial applications in form of corrosion inhibitions , dyes , and optical brightners .…”