Primary cycloadducts of 1,10-phenanthrolinium and phthalazinium phenacylides with DMAD

1,3-Dipolar cycloaddition reactions of 1-(3-nitrophenacyl)-1,10-phenanthrolinium N-ylide with activated alkynes

“…The behavior can be explained by non-coplanarity between pyrrolic and pyridinic moieties, rendering helical chirality to the molecules of 7b,c, at room temperature. 9 This behavior renders the molecular framework chiral, thereby explaining the non-equivalence of the diastereotopic methylene and methyl (in the isopropyl group) protons in the 1 H-NMR spectra. Recently, this hypothesis was confirmed by X-ray analysis.…”

“…[1][2][3][4][5] The dipolar 3+2 cycloaddition of dipolarophiles to heteroaromatic N-ylides raises interesting regio-and stereoselectivity problems. [5][6][7][8][9] Recently, the synthesis of a new heterocyclic system, namely pyrrolo[1,2-a] [1,10]phenanthroline, by 1,3-dipolar cycloaddition of 1,10-phenanthrolinium N-ylides with acetylenic dipolarophiles, was described. [9][10][11][12] The extended heteroaromatic system presents helical chirality, like that of the helicene-type compounds.…”

“…[5][6][7][8][9] Recently, the synthesis of a new heterocyclic system, namely pyrrolo[1,2-a] [1,10]phenanthroline, by 1,3-dipolar cycloaddition of 1,10-phenanthrolinium N-ylides with acetylenic dipolarophiles, was described. [9][10][11][12] The extended heteroaromatic system presents helical chirality, like that of the helicene-type compounds. 13 Herein we describe the reaction of 1-(3-nitrophenacyl)-1,10-phenanthrolinium N-ylide (4) with activated alkynes giving new pyrrolo [1,2- The structure of trans-5a was assigned on the basis of the coupling constants of the hydrogen atoms from the pyrroline and phenanthroline moieties, 1 H-NMR chemical shifts of CH and NCH groups, as well as 13 C-NMR chemical shifts of the carbonyl groups.…”

Pyrrolo[1,2-b]pyridazines. A revisit

“…Although the formation of 4a,7-dihydroderivatives of type 40 has been mentioned in many papers, no data was presented for the presence of these compound, as opposed to the case of phtalazinium Nylides. 104 Finally, the dihydroderivative is aromatized in the reaction conditions, but in some …”

New fluorescent indolizines and bisindolizinylethylenes

“…[5][6][7][8][9][10] One of the most recent developments is the use of such compounds in optoelectronic devices, mostly as pure-color luminophores in OLEDs (organic light emitting diodes). 11,12 Indolizine, resembling condensed pyridine and pyrrole rings, is the simplest pyrroloazine.…”