Chodkiewicz, Wladyslaw published the artcileAcetylenic monoquinols; preparation of diquinols and asymmetric polyacetylenic arenes, Quality Control of 18512-55-5, the publication is Compt. rend. (1958), 2383-5, database is CAplus.
Monocondensation of anthraquinone with true acetylenic compounds, RCCH, was carried out in the presence of NaNH2 in tetrahydrofuran or disubstituted amide solvents for 2-3 hrs. at -30° to 0° to give acetylenic monoquinols (I) as follows (R in RCCH, % yield, and m.p. of product given): H, 89, 235°; Me(CH2)4, 90, 130°; Ph, 83, 201°; Me2NCH2, 86, 215°; Ph2C(OH), 82, 198°; Ph2C(OH)CH2, 77, 172°. The monoquinol Me ethers (II) were obtained almost quant. from I and Me2SO4 in Et2O in the presence of powd. KOH. II with HCCH in tetrahydrofuran in the presence of KOH (30 min. to 1 hr. at 20°) gave the Me monoethers of the diquinols (III) (R, % yield, and m.p. given): Me(CH2)4, 98, 92°; Ph, 97, 143° and 164° (corresponding to 2 possible isomers); H, 70, 158°. Reduction of III in Et2O-MeOH-H2O with SnCl2 in the presence of H2SO4 gave 9-ethynyl-10-(R-substituted-ethynyl)anthracene (IV) (R, % yield, and m.p. given): Ph, 83, 170° (decomposition); H, 90, 107°. IV condensed with Ph2CO and KOH in tetrahydrofuran (5-30 min. at 20°) gave the 9-[CCC(Ph)2OH] analog (V) as follows (R, % yield, m.p. given): Ph, 98, 178°; H, 95, 149°. The 9-(OH)9-[CCC(Ph)2OH] 10-(:O) derivative of anthracene was reduced in Et2O with SnCl2 in the presence of AcCl to give 93% of the 9-(:C:C:CPh2) analog, m. 242°, the first representative of a new class of cumulenes in which the unsaturated system was conjugated with a carbonyl group.
Compt. rend. published new progress about 18512-55-5. 18512-55-5 belongs to naphthyridine, auxiliary class Alkynyl,Anthracene, name is 9,10-Diethynylanthracene, and the molecular formula is C18H10, Quality Control of 18512-55-5.
Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem