3-(N-CARBAZOLYL)PROPYNE

The mixture of carbazole (4.175 g, 25 mmol) and metallic sodium (0.575 g, 25 mmol) in dioxane (20 ml) was refluxed under inert atmosphere until metallic sodium was completely dissolved. Later, propargyl bromide (3.38 ml, 39 mmol) was added into the mixture. The solution was cooled to room temperature and stirred for 18 h. Finally, water was added and the mixture was extracted with CH2CI2. The organic phase was dried with NaSO4 and filtered. The solvent was removed under vacuum and the residue was purified by column chromatography (10:1 Hexane/Ethyl acetate) to yield 9-(prop-2-yn-1-yl)-9H-carbazole (percent76).General procedure: The benzofused N-heteroaromatic alkynes 2, 5, and 8 weresynthesized by reacting benzimidazole (1.0 mmol), benzotriazole (1.0 mmol), or carbazole (1.0 mmol) withpropargyl bromide (1.2 mmol) in the presence of potassiumcarbonate (2.0 mmol) using dimethylformamide bycontinuous stirring at 10–25 C up to 8–10 h [32]. For thesynthesis of target compounds, solution of aromatic bromides(1.0 mmol) in dimethylformamide was taken in around-bottomed flask and aqueous solution of sodium azide(3.0 mmol) was added, thereafter, stirred the reactionmixture for 1 h at 25–40 C. To the above reaction mixture, benzofused N-heteroaromatic alkyne 2 (1.0 mmol), 5(1.0 mmol), or 8 (1.0 mmol) was added followed by coppersulfate pentahydrate (5 mol percent) and sodium ascorbate(10 mol percent) [33], then, stirred the reaction contents overnight.The progress of reaction was monitored by thin layerchromatography. After the completion of reaction, ice-colddistilled water was added to the reaction mixture andproduct was extracted with ethyl acetate (50 cm3 9 3).The organic layer was washed with aqueous ammoniasolution followed by brine solution and dried using anhydroussodium sulfate. Filtered and evaporated the solventunder vacuum to get crude product which was furtherpurified by column chromatography using hexane:ethylacetate (7:3) as eluent.

Molecular Weight:205.25
XLogP3:3.6
Rotatable Bond Count:1
Exact Mass:205.089149355
Monoisotopic Mass:205.089149355
Topological Polar Surface Area:4.9
Heavy Atom Count:16
Complexity:278
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes