Synthesis of novel phenanthroline derivatives by 3+2 dipolar cycloadition reaction

Abstract

Eleven new 1,10-phenanthroline derivatives have been prepared by 3+2 dipolar cycloaddition reactions of 1,10-phenanthrolinium-ylides 7-12 in situ generated from corresponded salts, with dimethyl acetylenedicarboxylate and ethyl propiolate.

New indolizines with phenanthroline skeleton: Synthesis, structure, antimycobacterial and anticancer evaluation

“…This proved us the presumed position of the two protons (8 and 9, Scheme 1) and as well a trans configuration at C14-C15 level, Figure 2. [19,25]. Thus, in IR spectra of compounds 6, the absorption band corresponding to the C=O ester group appears at similar wave numbers (1714-1692 cm -1 ) as the ester group attached to C7 in compounds 4, proving the structure 6 of these compounds.…”

“…19,22 Because a single regioisomer is obtained, these types of reactions are considered highly regioselective under charge control in accordance with the usual electronic effects in dipolarophiles. In all reactions we assume that first, unisolable 9,15-dihydropyrrolo [1,[2][3][4] i] [1,7]phenanthroline intermediates type 3 are formed and then an oxidative aromatization takes place, giving policyclic indolizines 4a-g and 6a-g.…”

“…In order to synthesize the new indolizine derivatives with phenanthroline skeleton, we have used an adaptation of the method previously described by our group [19][20][21][22][23][24] in the case of some other indolizine derivatives: Huisgen [3+2] dipolar cycloaddition reactions of ylides (as 1,3-dipoles) to alkynes or alkenes (as dipolarophiles).…”

Synthesis of novel 4,5‐diazafluoren‐9‐one derivatives and theoretical study of 3+2 cycloaddition reactions

“…The 1 H nmr spectra were run on a BRUKER-300 spectrometer and were recorded in ppm downfield from an internal standard TMS in DMSO-d 6 for compounds 3a-e and in CDCl 3 for compounds 6a-e. The coupling constants are given in Hz.…”

“…There are many recent references in the literature related to the 3+2 cycloaddition reaction of cycloimmonium ylides to activated symmetrical or non-symmetrical olefins and alkynes [1][2][3][4][5][6]. These reactions are very interesting due to the possibility of preparing cycloadducts, which are difficult to obtain otherwise.…”