Haloheterocyclization of 2-allyl(propargyl)oxyquinoline-3-carbaldehydes

Abstract

There are literature reports of the haloheterocyclization reactions of unsaturated quinoline ethers and thioethers [1] to give heterocyclic systems with oxa(thia)zolinium rings. In continuation of these studies we have selected the 2-allyl(propargyl)oxyquinoline-3-carbaldehydes 3, 4 as model compounds for this haloheterocyclization. These substrates were prepared by conversion of 2-chloro-3-formylquinolines 1 to the corresponding quinolones 2 by treatment with hydrochloric acid and subsequent alkylation using allyl(propargyl) bromides. N R O Cl H 2 O, HCl N R O OH N H R O O N R O O X 2 R O N O X N R O O X 2 R O N O X X X 1a,b 2a,b + 3a,b 5, 6a,b + 4a,b 7, 8a,b KOH KOH CH 2 =CHCH 2 Br HC CCH 2 Br 1 2 3 4 5 6 7 8 -2n+1 -2n+1 1-8 a R = H, b R = Me; 5, 7 Х = Br, n = 0; 6, 8 X = I , n = 1

Crystal structure of (E)-3-(iodomethylene)-2,3-dihydro-[1,4]oxazino- [2,3,4-ij]quinolin-4-ium triodide —iodine (2:1), [C12H9INO]I3·0.5I2, C12H9I5NO

“…The title compound was synthesized in the context of obtaining new heteroaromatic systems by heterocyclization withanexcess of iodine [2]. Thepresented crystalstructure canbeaninteresting object with I×××In on-covalent interactions involving terminal triiodide atomsasdonors of electrons and iodine in I 2 molecule as electrophilic species.…”